teicoplanin A2-3

CHEBI:34996 EXACT SEEDED antimicrobial unspecified

What these status tags mean

Curation status describes a workflow state. SEEDED means the record entered through the source-seeding workflow; it does not imply that no later curation occurred. PROPOSED marks an addition awaiting review; REVIEWED records curator sign-off on identity, structure, filing class and producer claims; DEPRECATED retains a superseded or out-of-scope record. These are workflow decisions, not independently verified human review. Agent-assisted contributions may appear in the record history.

Grounding describes the identifier mapping: EXACT uses an ontology identity asserted by the source; MINTED keeps a local identifier when no defensible ontology identity is available; REVIEW_NEEDED flags an exact structure whose ontology identity needs adjudication. The grounding note retains any unresolved alternatives. These tags do not establish the strength of producer or activity evidence.

A teicoplanin A2 that has decanoyl as the variable N-acyl group.

Structure

Standard InChIKey	BJNLLBUOHPVGFT-PKMGYIMSSA-N
SMILES	CCCCCCCCCC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)[C@H]([C@H]6C(=O)N[C@@H](C7=CC(=CC(=C7C8=C(C=CC(=C8)[C@H](C(=O)N6)NC(=O)[C@@H]4NC(=O)[C@@H]9C1=CC(=CC(=C1)O)OC1=C(C=CC(=C1)[C@H](C(=O)N[C@H](CC1=CC(=C(O3)C=C1)Cl)C(=O)N9)N)O)O)O[C@@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)C(=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)NC(=O)C)Cl)CO)O)O
Stereochemistry	fully defined
Cross-references	npatlas:NPA020142

Filing pathway

Amino acids and peptides — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is nrps, from MIBiG.

Producer organisms 1

A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.

Taxon	Basis	Cluster	Evidence
Actinoplanes teichomyceticus NCBITaxon:1867	SOURCE_ASSERTION	mibig:BGC0000440	DOI:10.1016/0195-6701(86)90011-3

Occurrences 2

Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.

Taxon	Source	Reference
Actinoplanes teichomyceticus NCBITaxon:1867	LOTUS	DOI:10.1021/JA00329A044
Actinoplanes teichomyceticus NCBITaxon:1867	CHEBI	PMID:2977757

Biosynthetic gene clusters 1

Accession	Host	Locus evidence	Genome
mibig:BGC0000440	Actinoplanes teichomyceticus NCBITaxon:1867	CLUSTER_DEMONSTRATED	genbank:AJ605139.1

A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.

Biosynthesis curated

Written by a curator with claim-level evidence on each step; not derived from a source. This is what the rest of the record exists to support.

Step	Enzyme	Substrate → product	Evidence
1	GtfB teicoplanin aglycone glycosyltransferase UniProtKB:Q6ZZI3	ungrounded → ungrounded	DOI:10.1099/mic.0.26507-0
2	GtfA teicoplanin Bht6 glycosyltransferase UniProtKB:Q6ZZJ7	ungrounded → ungrounded	DOI:10.1099/mic.0.26507-0
3	Orf2* teicoplanin Hpg4 N-acetylglucosaminyl deacetylase UniProtKB:Q6ZZJ1	ungrounded → ungrounded	DOI:10.1021/ja0644834
4	Tcp24 teicoplanin Hpg4 N-acyltransferase UniProtKB:Q70AY4	ungrounded → ungrounded	DOI:10.1016/s1074-5521(04)00002-x

Step 1: GtfB/tcp23 transfers N-acetylglucosamine from UDP-N-acetyl-alpha-D-glucosamine to Hpg4 of the teicoplanin aglycone. That Hpg4 glycosylation precedes downstream deacetylation, acylation and tailoring toward teicoplanin A2-3, so the immediate pseudoaglycone product is left ungrounded.

Step 2: GtfA/tcp8 transfers N-acetylglucosamine from UDP-N-acetyl-alpha-D-glucosamine to Bht6/3-Cl-6betaHty of a GtfB-primed teicoplanin pseudoaglycone. GtfA can also glycosylate the unmodified teicoplanin aglycone less efficiently, but Bht6 glycosylation is ordered here after Hpg4 glycosylation toward teicoplanin A2-3, so the immediate bis-glycosylated product is left ungrounded.

Step 3: Orf2*/tcp14 deacetylates the Hpg4 N-acetylglucosaminyl group of the teicoplanin pseudoaglycone, exposing the Hpg4 glucosamine for downstream N-acylation toward teicoplanin A2-3.

Step 4: Tcp24/tAtf transfers a fatty acyl group from an acyl-CoA donor to the Orf2*-exposed Hpg4 glucosamine of the teicoplanin pseudoaglycone. The immediate N-acylated bis-glycosylated product is left ungrounded because the record-specific A2 lipid donor is not grounded here.

Mechanism & Biosynthesis Overview

Causal graph — biosynthesis 4 nodes, 3 edges

Actinoplanes teichomyceticus ATCC 31131 GtfB glycosylates Hpg4 of the teicoplanin aglycone with UDP-N-acetyl-alpha-D-glucosamine during teicoplanin A2 pseudoaglycone biosynthesis.

Subject	Predicate	Object	Evidence
teicoplanin aglycone	is Hpg4-glycosylated by	GtfB	DOI:10.1099/mic.0.26507-0 DOI:10.1016/s1074-5521(04)00002-x DOI:10.1021/ja0735857 https://mite.bioinformatics.nl/repository/MITE0000033 https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk https://www.uniprot.org/uniprotkb/Q6ZZI3 https://www.ncbi.nlm.nih.gov/protein/CAE53364.1 CHEBI:16264 reference DOI:10.1099/mic.0.26507-0 evidence type PRIMARY_EXPERIMENT snippet tGtfB can only glycosylate the teicoplanin aglycon notes Sosio et al. isolated the Actinoplanes teichomyceticus ATCC 31131 tcp cluster on AJ605139, assigned tcp23 as a GtfB glycosyltransferase, and characterized teicoplanin aglycone glycosylation in vitro. reference DOI:10.1016/s1074-5521(04)00002-x evidence type PRIMARY_EXPERIMENT snippet 4-hydroxyphenylglycine-4 (4Hpg) of the teicoplanin heptapeptide aglycone notes Li et al. cloned the 89 kbp teicoplanin biosynthetic locus and heterologously assayed its glycosyltransferases, including the enzyme that modifies Hpg4 of the teicoplanin aglycone. reference DOI:10.1021/ja0735857 evidence type PRIMARY_EXPERIMENT notes Howard-Jones et al. kinetically analyzed the teicoplanin glycosyltransferases and acyltransferase, supporting ordered tailoring of the aglycone scaffold during mature teicoplanin reconstitution. reference https://mite.bioinformatics.nl/repository/MITE0000033 evidence type DATABASE_ASSERTION snippet Adds N-acetylglucosamine or N-acylglucosamine to Hpg4 of the teicoplanin aglycone retrieved on 2026-10-03 notes MITE0000033 is active, records GtfB as a glycosyltransferase that modifies Hpg4 of the teicoplanin aglycone, and links GtfB to UniProtKB:Q6ZZI3, GenPept CAE53364.1 and MIBiG BGC0000440. reference https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk evidence type DATABASE_ASSERTION snippet MITE0000033: Glycosylation (100% identity) retrieved on 2026-10-03 notes MIBiG BGC0000440.5 places the Actinoplanes teichomyceticus tcp23 CDS at AJ605139.1:60486..61712 with GenPept protein_id CAE53364.1, UniProtKB/TrEMBL Q6ZZI3, and a 100% identity MITE0000033 glycosylation annotation. reference https://www.uniprot.org/uniprotkb/Q6ZZI3 evidence type DATABASE_ASSERTION snippet AC Q6ZZI3; retrieved on 2026-10-03 notes Current UniProtKB:Q6ZZI3 resolves to a 408 aa Actinoplanes teichomyceticus glycosyltransferase sequence whose sequence is identical to CAE53364.1. reference https://www.ncbi.nlm.nih.gov/protein/CAE53364.1 evidence type DATABASE_ASSERTION snippet /product="GtfB protein" retrieved on 2026-10-03 notes NCBI Protein CAE53364.1 is the 408 aa Actinoplanes teichomyceticus ATCC 31131 tcp23/GtfB protein translated from AJ605139.1:60486..61712 and cross-referenced to UniProtKB/TrEMBL Q6ZZI3. reference CHEBI:16264 evidence type DATABASE_ASSERTION retrieved on 2026-10-03 notes ChEBI:16264 is the 3-star ChEBI entry for UDP-N-acetyl-alpha-D-glucosamine, the UDP-amino-sugar donor used for GtfB-catalyzed N-acetylglucosamine transfer.
UDP-N-acetyl-alpha-D-glucosamine	donates N-acetylglucosamine via	GtfB	DOI:10.1099/mic.0.26507-0 DOI:10.1016/s1074-5521(04)00002-x DOI:10.1021/ja0735857 https://mite.bioinformatics.nl/repository/MITE0000033 https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk https://www.uniprot.org/uniprotkb/Q6ZZI3 https://www.ncbi.nlm.nih.gov/protein/CAE53364.1 CHEBI:16264 reference DOI:10.1099/mic.0.26507-0 evidence type PRIMARY_EXPERIMENT snippet tGtfB can only glycosylate the teicoplanin aglycon notes Sosio et al. isolated the Actinoplanes teichomyceticus ATCC 31131 tcp cluster on AJ605139, assigned tcp23 as a GtfB glycosyltransferase, and characterized teicoplanin aglycone glycosylation in vitro. reference DOI:10.1016/s1074-5521(04)00002-x evidence type PRIMARY_EXPERIMENT snippet 4-hydroxyphenylglycine-4 (4Hpg) of the teicoplanin heptapeptide aglycone notes Li et al. cloned the 89 kbp teicoplanin biosynthetic locus and heterologously assayed its glycosyltransferases, including the enzyme that modifies Hpg4 of the teicoplanin aglycone. reference DOI:10.1021/ja0735857 evidence type PRIMARY_EXPERIMENT notes Howard-Jones et al. kinetically analyzed the teicoplanin glycosyltransferases and acyltransferase, supporting ordered tailoring of the aglycone scaffold during mature teicoplanin reconstitution. reference https://mite.bioinformatics.nl/repository/MITE0000033 evidence type DATABASE_ASSERTION snippet Adds N-acetylglucosamine or N-acylglucosamine to Hpg4 of the teicoplanin aglycone retrieved on 2026-10-03 notes MITE0000033 is active, records GtfB as a glycosyltransferase that modifies Hpg4 of the teicoplanin aglycone, and links GtfB to UniProtKB:Q6ZZI3, GenPept CAE53364.1 and MIBiG BGC0000440. reference https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk evidence type DATABASE_ASSERTION snippet MITE0000033: Glycosylation (100% identity) retrieved on 2026-10-03 notes MIBiG BGC0000440.5 places the Actinoplanes teichomyceticus tcp23 CDS at AJ605139.1:60486..61712 with GenPept protein_id CAE53364.1, UniProtKB/TrEMBL Q6ZZI3, and a 100% identity MITE0000033 glycosylation annotation. reference https://www.uniprot.org/uniprotkb/Q6ZZI3 evidence type DATABASE_ASSERTION snippet AC Q6ZZI3; retrieved on 2026-10-03 notes Current UniProtKB:Q6ZZI3 resolves to a 408 aa Actinoplanes teichomyceticus glycosyltransferase sequence whose sequence is identical to CAE53364.1. reference https://www.ncbi.nlm.nih.gov/protein/CAE53364.1 evidence type DATABASE_ASSERTION snippet /product="GtfB protein" retrieved on 2026-10-03 notes NCBI Protein CAE53364.1 is the 408 aa Actinoplanes teichomyceticus ATCC 31131 tcp23/GtfB protein translated from AJ605139.1:60486..61712 and cross-referenced to UniProtKB/TrEMBL Q6ZZI3. reference CHEBI:16264 evidence type DATABASE_ASSERTION retrieved on 2026-10-03 notes ChEBI:16264 is the 3-star ChEBI entry for UDP-N-acetyl-alpha-D-glucosamine, the UDP-amino-sugar donor used for GtfB-catalyzed N-acetylglucosamine transfer.
GtfB	forms	Hpg4 N-acetylglucosaminyl teicoplanin pseudoaglycone	DOI:10.1099/mic.0.26507-0 DOI:10.1016/s1074-5521(04)00002-x DOI:10.1021/ja0735857 https://mite.bioinformatics.nl/repository/MITE0000033 https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk https://www.uniprot.org/uniprotkb/Q6ZZI3 https://www.ncbi.nlm.nih.gov/protein/CAE53364.1 CHEBI:16264 reference DOI:10.1099/mic.0.26507-0 evidence type PRIMARY_EXPERIMENT snippet tGtfB can only glycosylate the teicoplanin aglycon notes Sosio et al. isolated the Actinoplanes teichomyceticus ATCC 31131 tcp cluster on AJ605139, assigned tcp23 as a GtfB glycosyltransferase, and characterized teicoplanin aglycone glycosylation in vitro. reference DOI:10.1016/s1074-5521(04)00002-x evidence type PRIMARY_EXPERIMENT snippet 4-hydroxyphenylglycine-4 (4Hpg) of the teicoplanin heptapeptide aglycone notes Li et al. cloned the 89 kbp teicoplanin biosynthetic locus and heterologously assayed its glycosyltransferases, including the enzyme that modifies Hpg4 of the teicoplanin aglycone. reference DOI:10.1021/ja0735857 evidence type PRIMARY_EXPERIMENT notes Howard-Jones et al. kinetically analyzed the teicoplanin glycosyltransferases and acyltransferase, supporting ordered tailoring of the aglycone scaffold during mature teicoplanin reconstitution. reference https://mite.bioinformatics.nl/repository/MITE0000033 evidence type DATABASE_ASSERTION snippet Adds N-acetylglucosamine or N-acylglucosamine to Hpg4 of the teicoplanin aglycone retrieved on 2026-10-03 notes MITE0000033 is active, records GtfB as a glycosyltransferase that modifies Hpg4 of the teicoplanin aglycone, and links GtfB to UniProtKB:Q6ZZI3, GenPept CAE53364.1 and MIBiG BGC0000440. reference https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk evidence type DATABASE_ASSERTION snippet MITE0000033: Glycosylation (100% identity) retrieved on 2026-10-03 notes MIBiG BGC0000440.5 places the Actinoplanes teichomyceticus tcp23 CDS at AJ605139.1:60486..61712 with GenPept protein_id CAE53364.1, UniProtKB/TrEMBL Q6ZZI3, and a 100% identity MITE0000033 glycosylation annotation. reference https://www.uniprot.org/uniprotkb/Q6ZZI3 evidence type DATABASE_ASSERTION snippet AC Q6ZZI3; retrieved on 2026-10-03 notes Current UniProtKB:Q6ZZI3 resolves to a 408 aa Actinoplanes teichomyceticus glycosyltransferase sequence whose sequence is identical to CAE53364.1. reference https://www.ncbi.nlm.nih.gov/protein/CAE53364.1 evidence type DATABASE_ASSERTION snippet /product="GtfB protein" retrieved on 2026-10-03 notes NCBI Protein CAE53364.1 is the 408 aa Actinoplanes teichomyceticus ATCC 31131 tcp23/GtfB protein translated from AJ605139.1:60486..61712 and cross-referenced to UniProtKB/TrEMBL Q6ZZI3. reference CHEBI:16264 evidence type DATABASE_ASSERTION retrieved on 2026-10-03 notes ChEBI:16264 is the 3-star ChEBI entry for UDP-N-acetyl-alpha-D-glucosamine, the UDP-amino-sugar donor used for GtfB-catalyzed N-acetylglucosamine transfer.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Causal graph — biosynthesis 4 nodes, 3 edges

Actinoplanes teichomyceticus ATCC 31131 GtfA glycosylates Bht6 of a GtfB-primed teicoplanin pseudoaglycone with UDP-N-acetyl-alpha-D-glucosamine during teicoplanin A2 pseudoaglycone biosynthesis.

Subject	Predicate	Object	Evidence
Hpg4 N-acetylglucosaminyl teicoplanin pseudoaglycone	is Bht6-glycosylated by	GtfA	DOI:10.1099/mic.0.26507-0 DOI:10.1016/s1074-5521(04)00002-x DOI:10.1021/ja0735857 https://mite.bioinformatics.nl/repository/MITE0000034 https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk https://www.uniprot.org/uniprotkb/Q6ZZJ7 https://www.ncbi.nlm.nih.gov/protein/CAE53349.1 CHEBI:16264 reference DOI:10.1099/mic.0.26507-0 evidence type PRIMARY_EXPERIMENT snippet tGtfA can add a sugar residue in the presence or absence of N-acetylglucosamine at amino acid 4 notes Sosio et al. isolated the Actinoplanes teichomyceticus ATCC 31131 tcp cluster on AJ605139, assigned tcp8 as a GtfA glycosyltransferase, and characterized teicoplanin amino-sugar transfer in vitro. reference DOI:10.1016/s1074-5521(04)00002-x evidence type PRIMARY_EXPERIMENT snippet 3-chloro-beta-hydroxytyrosine-6 (3-Cl-6betaHty) and 4-hydroxyphenylglycine-4 (4Hpg) notes Li et al. cloned the 89 kbp teicoplanin biosynthetic locus and heterologously assayed its glycosyltransferases, including the enzyme that modifies 3-Cl-6betaHty/Bht6 of the teicoplanin aglycone. reference DOI:10.1021/ja0735857 evidence type PRIMARY_EXPERIMENT notes Howard-Jones et al. kinetically analyzed the teicoplanin glycosyltransferases and acyltransferase, supporting ordered tailoring of the aglycone scaffold during mature teicoplanin reconstitution. reference https://mite.bioinformatics.nl/repository/MITE0000034 evidence type DATABASE_ASSERTION snippet Glycosyltransferase adds N-acetylglucosamine to Bht6 of the teicoplanin precursor retrieved on 2026-10-03 notes MITE0000034 is active, records GtfA as a glycosyltransferase that modifies Bht6 of the teicoplanin precursor, and links GtfA to UniProtKB:Q6ZZJ7, GenPept CAE53349.1 and MIBiG BGC0000440. reference https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk evidence type DATABASE_ASSERTION snippet MITE0000034: Glycosylation (100% identity) retrieved on 2026-10-03 notes MIBiG BGC0000440.5 places the Actinoplanes teichomyceticus tcp8 CDS at AJ605139.1:18949..20130 with GenPept protein_id CAE53349.1, UniProtKB/TrEMBL Q6ZZJ7, and a 100% identity MITE0000034 glycosylation annotation. reference https://www.uniprot.org/uniprotkb/Q6ZZJ7 evidence type DATABASE_ASSERTION snippet AC Q6ZZJ7; retrieved on 2026-10-03 notes Current UniProtKB:Q6ZZJ7 resolves to a 393 aa Actinoplanes teichomyceticus GtfA sequence whose sequence is identical to CAE53349.1. reference https://www.ncbi.nlm.nih.gov/protein/CAE53349.1 evidence type DATABASE_ASSERTION snippet /product="GtfA protein" retrieved on 2026-10-03 notes NCBI Protein CAE53349.1 is the 393 aa Actinoplanes teichomyceticus tcp8/GtfA protein translated from AJ605139.1:18949..20130 and cross-referenced to UniProtKB/TrEMBL Q6ZZJ7. reference CHEBI:16264 evidence type DATABASE_ASSERTION retrieved on 2026-10-03 notes ChEBI:16264 is the 3-star ChEBI entry for UDP-N-acetyl-alpha-D-glucosamine, the UDP-amino-sugar donor used for GtfA-catalyzed N-acetylglucosamine transfer.
UDP-N-acetyl-alpha-D-glucosamine	donates N-acetylglucosamine via	GtfA	DOI:10.1099/mic.0.26507-0 DOI:10.1016/s1074-5521(04)00002-x DOI:10.1021/ja0735857 https://mite.bioinformatics.nl/repository/MITE0000034 https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk https://www.uniprot.org/uniprotkb/Q6ZZJ7 https://www.ncbi.nlm.nih.gov/protein/CAE53349.1 CHEBI:16264 reference DOI:10.1099/mic.0.26507-0 evidence type PRIMARY_EXPERIMENT snippet tGtfA can add a sugar residue in the presence or absence of N-acetylglucosamine at amino acid 4 notes Sosio et al. isolated the Actinoplanes teichomyceticus ATCC 31131 tcp cluster on AJ605139, assigned tcp8 as a GtfA glycosyltransferase, and characterized teicoplanin amino-sugar transfer in vitro. reference DOI:10.1016/s1074-5521(04)00002-x evidence type PRIMARY_EXPERIMENT snippet 3-chloro-beta-hydroxytyrosine-6 (3-Cl-6betaHty) and 4-hydroxyphenylglycine-4 (4Hpg) notes Li et al. cloned the 89 kbp teicoplanin biosynthetic locus and heterologously assayed its glycosyltransferases, including the enzyme that modifies 3-Cl-6betaHty/Bht6 of the teicoplanin aglycone. reference DOI:10.1021/ja0735857 evidence type PRIMARY_EXPERIMENT notes Howard-Jones et al. kinetically analyzed the teicoplanin glycosyltransferases and acyltransferase, supporting ordered tailoring of the aglycone scaffold during mature teicoplanin reconstitution. reference https://mite.bioinformatics.nl/repository/MITE0000034 evidence type DATABASE_ASSERTION snippet Glycosyltransferase adds N-acetylglucosamine to Bht6 of the teicoplanin precursor retrieved on 2026-10-03 notes MITE0000034 is active, records GtfA as a glycosyltransferase that modifies Bht6 of the teicoplanin precursor, and links GtfA to UniProtKB:Q6ZZJ7, GenPept CAE53349.1 and MIBiG BGC0000440. reference https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk evidence type DATABASE_ASSERTION snippet MITE0000034: Glycosylation (100% identity) retrieved on 2026-10-03 notes MIBiG BGC0000440.5 places the Actinoplanes teichomyceticus tcp8 CDS at AJ605139.1:18949..20130 with GenPept protein_id CAE53349.1, UniProtKB/TrEMBL Q6ZZJ7, and a 100% identity MITE0000034 glycosylation annotation. reference https://www.uniprot.org/uniprotkb/Q6ZZJ7 evidence type DATABASE_ASSERTION snippet AC Q6ZZJ7; retrieved on 2026-10-03 notes Current UniProtKB:Q6ZZJ7 resolves to a 393 aa Actinoplanes teichomyceticus GtfA sequence whose sequence is identical to CAE53349.1. reference https://www.ncbi.nlm.nih.gov/protein/CAE53349.1 evidence type DATABASE_ASSERTION snippet /product="GtfA protein" retrieved on 2026-10-03 notes NCBI Protein CAE53349.1 is the 393 aa Actinoplanes teichomyceticus tcp8/GtfA protein translated from AJ605139.1:18949..20130 and cross-referenced to UniProtKB/TrEMBL Q6ZZJ7. reference CHEBI:16264 evidence type DATABASE_ASSERTION retrieved on 2026-10-03 notes ChEBI:16264 is the 3-star ChEBI entry for UDP-N-acetyl-alpha-D-glucosamine, the UDP-amino-sugar donor used for GtfA-catalyzed N-acetylglucosamine transfer.
GtfA	forms	Hpg4/Bht6 bis-N-acetylglucosaminyl teicoplanin pseudoaglycone	DOI:10.1099/mic.0.26507-0 DOI:10.1016/s1074-5521(04)00002-x DOI:10.1021/ja0735857 https://mite.bioinformatics.nl/repository/MITE0000034 https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk https://www.uniprot.org/uniprotkb/Q6ZZJ7 https://www.ncbi.nlm.nih.gov/protein/CAE53349.1 CHEBI:16264 reference DOI:10.1099/mic.0.26507-0 evidence type PRIMARY_EXPERIMENT snippet tGtfA can add a sugar residue in the presence or absence of N-acetylglucosamine at amino acid 4 notes Sosio et al. isolated the Actinoplanes teichomyceticus ATCC 31131 tcp cluster on AJ605139, assigned tcp8 as a GtfA glycosyltransferase, and characterized teicoplanin amino-sugar transfer in vitro. reference DOI:10.1016/s1074-5521(04)00002-x evidence type PRIMARY_EXPERIMENT snippet 3-chloro-beta-hydroxytyrosine-6 (3-Cl-6betaHty) and 4-hydroxyphenylglycine-4 (4Hpg) notes Li et al. cloned the 89 kbp teicoplanin biosynthetic locus and heterologously assayed its glycosyltransferases, including the enzyme that modifies 3-Cl-6betaHty/Bht6 of the teicoplanin aglycone. reference DOI:10.1021/ja0735857 evidence type PRIMARY_EXPERIMENT notes Howard-Jones et al. kinetically analyzed the teicoplanin glycosyltransferases and acyltransferase, supporting ordered tailoring of the aglycone scaffold during mature teicoplanin reconstitution. reference https://mite.bioinformatics.nl/repository/MITE0000034 evidence type DATABASE_ASSERTION snippet Glycosyltransferase adds N-acetylglucosamine to Bht6 of the teicoplanin precursor retrieved on 2026-10-03 notes MITE0000034 is active, records GtfA as a glycosyltransferase that modifies Bht6 of the teicoplanin precursor, and links GtfA to UniProtKB:Q6ZZJ7, GenPept CAE53349.1 and MIBiG BGC0000440. reference https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk evidence type DATABASE_ASSERTION snippet MITE0000034: Glycosylation (100% identity) retrieved on 2026-10-03 notes MIBiG BGC0000440.5 places the Actinoplanes teichomyceticus tcp8 CDS at AJ605139.1:18949..20130 with GenPept protein_id CAE53349.1, UniProtKB/TrEMBL Q6ZZJ7, and a 100% identity MITE0000034 glycosylation annotation. reference https://www.uniprot.org/uniprotkb/Q6ZZJ7 evidence type DATABASE_ASSERTION snippet AC Q6ZZJ7; retrieved on 2026-10-03 notes Current UniProtKB:Q6ZZJ7 resolves to a 393 aa Actinoplanes teichomyceticus GtfA sequence whose sequence is identical to CAE53349.1. reference https://www.ncbi.nlm.nih.gov/protein/CAE53349.1 evidence type DATABASE_ASSERTION snippet /product="GtfA protein" retrieved on 2026-10-03 notes NCBI Protein CAE53349.1 is the 393 aa Actinoplanes teichomyceticus tcp8/GtfA protein translated from AJ605139.1:18949..20130 and cross-referenced to UniProtKB/TrEMBL Q6ZZJ7. reference CHEBI:16264 evidence type DATABASE_ASSERTION retrieved on 2026-10-03 notes ChEBI:16264 is the 3-star ChEBI entry for UDP-N-acetyl-alpha-D-glucosamine, the UDP-amino-sugar donor used for GtfA-catalyzed N-acetylglucosamine transfer.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Causal graph — biosynthesis 3 nodes, 2 edges

Actinoplanes teichomyceticus ATCC 31131 Orf2*/tcp14 deacetylates the Hpg4 N-acetylglucosaminyl group of the bis-glycosylated teicoplanin pseudoaglycone during teicoplanin A2 maturation.

Subject	Predicate	Object	Notes	Evidence
Hpg4/Bht6 bis-N-acetylglucosaminyl teicoplanin pseudoaglycone	is Hpg4-deacetylated by	Orf2*		DOI:10.1021/ja0644834 DOI:10.1002/cbic.200600308 DOI:10.1016/j.chembiol.2008.05.009 https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk https://www.uniprot.org/uniprotkb/Q6ZZJ1 https://www.ncbi.nlm.nih.gov/protein/CAE53355.1 reference DOI:10.1021/ja0644834 evidence type PRIMARY_EXPERIMENT snippet Orf2* catalyze the deacetylation reaction notes Ho et al. biochemically assigned Actinoplanes teichomyceticus Orf2* as the N-acetylglucosaminyl-teicoplanin pseudoaglycone deacetylase that prepares the Hpg4 sugar for downstream N-acylation. reference DOI:10.1002/cbic.200600308 evidence type PRIMARY_EXPERIMENT notes Truman et al. independently identified Orf2* as a teicoplanin maturation deacetylase and amplified the orf2* gene from the T4B2 cosmid of the cloned teicoplanin cluster for in vitro expression. reference DOI:10.1016/j.chembiol.2008.05.009 evidence type PRIMARY_EXPERIMENT snippet pseudoaglycone deacetylases from the biosynthetic pathways of teicoplanin and A40926 notes Zou et al. solved crystal structures of the Actinoplanes teichomyceticus teicoplanin pseudoaglycone deacetylase, supporting the Orf2/tcp14 protein-level assignment. reference https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk evidence type DATABASE_ASSERTION snippet /db_xref="UniProtKB/TrEMBL:Q6ZZJ1" retrieved on 2026-10-03 notes MIBiG BGC0000440.5 places the Actinoplanes teichomyceticus tcp14 CDS at AJ605139.1:48426..49247 with GenPept protein_id CAE53355.1 and UniProtKB/TrEMBL Q6ZZJ1. reference https://www.uniprot.org/uniprotkb/Q6ZZJ1 evidence type DATABASE_ASSERTION snippet AC Q6ZZJ1; retrieved on 2026-10-03 notes Current UniProtKB:Q6ZZJ1 resolves to a 273 aa Actinoplanes teichomyceticus tcp14 sequence whose sequence is identical to CAE53355.1 and whose PDB mappings cover Orf2 deacetylase structures. reference https://www.ncbi.nlm.nih.gov/protein/CAE53355.1 evidence type DATABASE_ASSERTION snippet /gene="tcp14" retrieved on 2026-10-03 notes NCBI Protein CAE53355.1 is the 273 aa Actinoplanes teichomyceticus ATCC 31131 tcp14 protein translated from AJ605139.1:48426..49247 and cross-referenced to UniProtKB/TrEMBL Q6ZZJ1.
Orf2*	forms	Hpg4 glucosaminyl/Bht6 N-acetylglucosaminyl teicoplanin pseudoaglycone		DOI:10.1021/ja0644834 DOI:10.1002/cbic.200600308 DOI:10.1016/j.chembiol.2008.05.009 https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk https://www.uniprot.org/uniprotkb/Q6ZZJ1 https://www.ncbi.nlm.nih.gov/protein/CAE53355.1 reference DOI:10.1021/ja0644834 evidence type PRIMARY_EXPERIMENT snippet Orf2* catalyze the deacetylation reaction notes Ho et al. biochemically assigned Actinoplanes teichomyceticus Orf2* as the N-acetylglucosaminyl-teicoplanin pseudoaglycone deacetylase that prepares the Hpg4 sugar for downstream N-acylation. reference DOI:10.1002/cbic.200600308 evidence type PRIMARY_EXPERIMENT notes Truman et al. independently identified Orf2* as a teicoplanin maturation deacetylase and amplified the orf2* gene from the T4B2 cosmid of the cloned teicoplanin cluster for in vitro expression. reference DOI:10.1016/j.chembiol.2008.05.009 evidence type PRIMARY_EXPERIMENT snippet pseudoaglycone deacetylases from the biosynthetic pathways of teicoplanin and A40926 notes Zou et al. solved crystal structures of the Actinoplanes teichomyceticus teicoplanin pseudoaglycone deacetylase, supporting the Orf2/tcp14 protein-level assignment. reference https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk evidence type DATABASE_ASSERTION snippet /db_xref="UniProtKB/TrEMBL:Q6ZZJ1" retrieved on 2026-10-03 notes MIBiG BGC0000440.5 places the Actinoplanes teichomyceticus tcp14 CDS at AJ605139.1:48426..49247 with GenPept protein_id CAE53355.1 and UniProtKB/TrEMBL Q6ZZJ1. reference https://www.uniprot.org/uniprotkb/Q6ZZJ1 evidence type DATABASE_ASSERTION snippet AC Q6ZZJ1; retrieved on 2026-10-03 notes Current UniProtKB:Q6ZZJ1 resolves to a 273 aa Actinoplanes teichomyceticus tcp14 sequence whose sequence is identical to CAE53355.1 and whose PDB mappings cover Orf2 deacetylase structures. reference https://www.ncbi.nlm.nih.gov/protein/CAE53355.1 evidence type DATABASE_ASSERTION snippet /gene="tcp14" retrieved on 2026-10-03 notes NCBI Protein CAE53355.1 is the 273 aa Actinoplanes teichomyceticus ATCC 31131 tcp14 protein translated from AJ605139.1:48426..49247 and cross-referenced to UniProtKB/TrEMBL Q6ZZJ1.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Causal graph — biosynthesis 4 nodes, 3 edges

Actinoplanes teichomyceticus ATCC 31131 Tcp24/tAtf N-acylates the Hpg4 glucosamine of the deacetylated teicoplanin pseudoaglycone during teicoplanin A2 maturation.

Subject	Predicate	Object	Evidence
Hpg4 glucosaminyl/Bht6 N-acetylglucosaminyl teicoplanin pseudoaglycone	is Hpg4-N-acylated by	Tcp24	DOI:10.1016/s1074-5521(04)00002-x DOI:10.1016/j.chembiol.2004.12.005 DOI:10.1021/ja0735857 https://mite.bioinformatics.nl/repository/MITE0000035 https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk https://www.uniprot.org/uniprotkb/Q70AY4 https://www.ncbi.nlm.nih.gov/protein/CAE53365.1 reference DOI:10.1016/s1074-5521(04)00002-x evidence type PRIMARY_EXPERIMENT notes Li et al. cloned the 89 kbp teicoplanin biosynthetic locus and heterologously assayed the key tAtf acyltransferase that acylates the Hpg4 glucosaminyl group. reference DOI:10.1016/j.chembiol.2004.12.005 evidence type PRIMARY_EXPERIMENT snippet responsible for N-acylation of the glucosamine moiety notes Kruger et al. evaluated purified teicoplanin acyltransferase tAtf with glycopeptide scaffolds and acyl-CoA donors, supporting direct Tcp24/tAtf N-acyl transfer. reference DOI:10.1021/ja0735857 evidence type PRIMARY_EXPERIMENT notes Howard-Jones et al. kinetically showed that tAtf strongly prefers aglycone-tethered 4-(2-aminoglucosyl)-teicoplanin over free UDP-2-aminoglucose for N-acylation. reference https://mite.bioinformatics.nl/repository/MITE0000035 evidence type DATABASE_ASSERTION snippet The highest catalytic efficiency of the enzyme is achieved with the glucosaminyl-teicoplanin pseudoaglycone as substrate. retrieved on 2026-10-03 notes MITE0000035 is active and links Tcp24/tAtf to UniProtKB:Q70AY4, GenPept CAE53365.1 and MIBiG BGC0000440. The entry also includes Orf2* deacetylation reactions merged from retired MITE0000036, so only its acylation reaction is used for Tcp24/tAtf. reference https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk evidence type DATABASE_ASSERTION snippet MITE0000035: Acylation, Hydrolysis (100% identity) retrieved on 2026-10-03 notes MIBiG BGC0000440.5 places the Actinoplanes teichomyceticus tcp24 CDS at AJ605139.1:61858..62829 with GenPept protein_id CAE53365.1, UniProtKB/TrEMBL Q70AY4, and a 100% identity MITE0000035 annotation. reference https://www.uniprot.org/uniprotkb/Q70AY4 evidence type DATABASE_ASSERTION snippet AC Q70AY4; retrieved on 2026-10-03 notes Current UniProtKB:Q70AY4 resolves to a 323 aa Actinoplanes teichomyceticus tcp24 sequence whose sequence is identical to CAE53365.1. reference https://www.ncbi.nlm.nih.gov/protein/CAE53365.1 evidence type DATABASE_ASSERTION snippet /gene="tcp24" retrieved on 2026-10-03 notes NCBI Protein CAE53365.1 is the 323 aa Actinoplanes teichomyceticus ATCC 31131 tcp24 protein translated from AJ605139.1:61858..62829 and cross-referenced to UniProtKB/TrEMBL Q70AY4.
fatty acyl-CoA donor	donates fatty acyl group via	Tcp24	DOI:10.1016/s1074-5521(04)00002-x DOI:10.1016/j.chembiol.2004.12.005 DOI:10.1021/ja0735857 https://mite.bioinformatics.nl/repository/MITE0000035 https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk https://www.uniprot.org/uniprotkb/Q70AY4 https://www.ncbi.nlm.nih.gov/protein/CAE53365.1 reference DOI:10.1016/s1074-5521(04)00002-x evidence type PRIMARY_EXPERIMENT notes Li et al. cloned the 89 kbp teicoplanin biosynthetic locus and heterologously assayed the key tAtf acyltransferase that acylates the Hpg4 glucosaminyl group. reference DOI:10.1016/j.chembiol.2004.12.005 evidence type PRIMARY_EXPERIMENT snippet responsible for N-acylation of the glucosamine moiety notes Kruger et al. evaluated purified teicoplanin acyltransferase tAtf with glycopeptide scaffolds and acyl-CoA donors, supporting direct Tcp24/tAtf N-acyl transfer. reference DOI:10.1021/ja0735857 evidence type PRIMARY_EXPERIMENT notes Howard-Jones et al. kinetically showed that tAtf strongly prefers aglycone-tethered 4-(2-aminoglucosyl)-teicoplanin over free UDP-2-aminoglucose for N-acylation. reference https://mite.bioinformatics.nl/repository/MITE0000035 evidence type DATABASE_ASSERTION snippet The highest catalytic efficiency of the enzyme is achieved with the glucosaminyl-teicoplanin pseudoaglycone as substrate. retrieved on 2026-10-03 notes MITE0000035 is active and links Tcp24/tAtf to UniProtKB:Q70AY4, GenPept CAE53365.1 and MIBiG BGC0000440. The entry also includes Orf2* deacetylation reactions merged from retired MITE0000036, so only its acylation reaction is used for Tcp24/tAtf. reference https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk evidence type DATABASE_ASSERTION snippet MITE0000035: Acylation, Hydrolysis (100% identity) retrieved on 2026-10-03 notes MIBiG BGC0000440.5 places the Actinoplanes teichomyceticus tcp24 CDS at AJ605139.1:61858..62829 with GenPept protein_id CAE53365.1, UniProtKB/TrEMBL Q70AY4, and a 100% identity MITE0000035 annotation. reference https://www.uniprot.org/uniprotkb/Q70AY4 evidence type DATABASE_ASSERTION snippet AC Q70AY4; retrieved on 2026-10-03 notes Current UniProtKB:Q70AY4 resolves to a 323 aa Actinoplanes teichomyceticus tcp24 sequence whose sequence is identical to CAE53365.1. reference https://www.ncbi.nlm.nih.gov/protein/CAE53365.1 evidence type DATABASE_ASSERTION snippet /gene="tcp24" retrieved on 2026-10-03 notes NCBI Protein CAE53365.1 is the 323 aa Actinoplanes teichomyceticus ATCC 31131 tcp24 protein translated from AJ605139.1:61858..62829 and cross-referenced to UniProtKB/TrEMBL Q70AY4.
Tcp24	forms	Hpg4 N-acylglucosaminyl/Bht6 N-acetylglucosaminyl teicoplanin pseudoaglycone	DOI:10.1016/s1074-5521(04)00002-x DOI:10.1016/j.chembiol.2004.12.005 DOI:10.1021/ja0735857 https://mite.bioinformatics.nl/repository/MITE0000035 https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk https://www.uniprot.org/uniprotkb/Q70AY4 https://www.ncbi.nlm.nih.gov/protein/CAE53365.1 reference DOI:10.1016/s1074-5521(04)00002-x evidence type PRIMARY_EXPERIMENT notes Li et al. cloned the 89 kbp teicoplanin biosynthetic locus and heterologously assayed the key tAtf acyltransferase that acylates the Hpg4 glucosaminyl group. reference DOI:10.1016/j.chembiol.2004.12.005 evidence type PRIMARY_EXPERIMENT snippet responsible for N-acylation of the glucosamine moiety notes Kruger et al. evaluated purified teicoplanin acyltransferase tAtf with glycopeptide scaffolds and acyl-CoA donors, supporting direct Tcp24/tAtf N-acyl transfer. reference DOI:10.1021/ja0735857 evidence type PRIMARY_EXPERIMENT notes Howard-Jones et al. kinetically showed that tAtf strongly prefers aglycone-tethered 4-(2-aminoglucosyl)-teicoplanin over free UDP-2-aminoglucose for N-acylation. reference https://mite.bioinformatics.nl/repository/MITE0000035 evidence type DATABASE_ASSERTION snippet The highest catalytic efficiency of the enzyme is achieved with the glucosaminyl-teicoplanin pseudoaglycone as substrate. retrieved on 2026-10-03 notes MITE0000035 is active and links Tcp24/tAtf to UniProtKB:Q70AY4, GenPept CAE53365.1 and MIBiG BGC0000440. The entry also includes Orf2* deacetylation reactions merged from retired MITE0000036, so only its acylation reaction is used for Tcp24/tAtf. reference https://mibig.secondarymetabolites.org/repository/BGC0000440.5/BGC0000440.gbk evidence type DATABASE_ASSERTION snippet MITE0000035: Acylation, Hydrolysis (100% identity) retrieved on 2026-10-03 notes MIBiG BGC0000440.5 places the Actinoplanes teichomyceticus tcp24 CDS at AJ605139.1:61858..62829 with GenPept protein_id CAE53365.1, UniProtKB/TrEMBL Q70AY4, and a 100% identity MITE0000035 annotation. reference https://www.uniprot.org/uniprotkb/Q70AY4 evidence type DATABASE_ASSERTION snippet AC Q70AY4; retrieved on 2026-10-03 notes Current UniProtKB:Q70AY4 resolves to a 323 aa Actinoplanes teichomyceticus tcp24 sequence whose sequence is identical to CAE53365.1. reference https://www.ncbi.nlm.nih.gov/protein/CAE53365.1 evidence type DATABASE_ASSERTION snippet /gene="tcp24" retrieved on 2026-10-03 notes NCBI Protein CAE53365.1 is the 323 aa Actinoplanes teichomyceticus ATCC 31131 tcp24 protein translated from AJ605139.1:61858..62829 and cross-referenced to UniProtKB/TrEMBL Q70AY4.

Every edge carries its own citation; an uncited edge is refused by the corpus tests.

Elsewhere in the fleet

AntibioticMech — CHEBI:34996 (same structure, same inchikey)

Explore across X-Mech

AntibioticMech (teicoplanin A2-3) ↗ MediaIngredientMech (CHEBI:34996) ↗ TaxonMech: Actinoplanes teichomyceticus (NCBITaxon:1867) ↗ PathwayMech (mibig:BGC0000440) ↗

Provenance

Source concept	Source	Version
BGC0000440	MIBIG	5
CHEBI:34996	CHEBI	3-star

This page is generated from data/natural_products/amino_acids_and_peptides/teicoplanin-a2-3.yaml, which is generated from the committed inventories. Neither is edited by hand.