Ansamitocin : Cluster information
Compound
Entry name | Ansamitocin |
---|---|
PKS Type | TypeI modular |
Starter Unit | 3-amino-5-hydroxybenzoic acid (AHBA) |
Chain Length | 8 |
Sugar Unit | none |
Classification | Ansamycin |
Activity | Antifungal Antitumor |
Composition | P-3: C32H43ClN2O9 |
Original source
Organism | Actinosynnema pretiosum subsp. auranticum |
---|---|
Strain | ATCC 31565 |
Contig | AF453501 U33059 |
PKS/NRPS Module
Ansam_00270 asmA | 0 | ||
1 | methylmalonyl-CoA | ||
2 | malonyl-CoA | ||
Ansam_00280 asmB | 3 | methoxymalonyl-ACP | |
4 | malonyl-CoA | ||
Ansam_00090 asmC | 5 | methylmalonyl-CoA | |
Ansam_00100 asmD | 6 | methylmalonyl-CoA | |
7 | malonyl-CoA |
Reference
- Identification of a set of genes involved in the formation of the substrate for the incorporation of the unusual "glycolate" chain extension unit in ansamitocin biosynthesis.
- Carroll BJ, Moss SJ, Bai L, Kato Y, Toelzer S, Yu TW, Floss HG[PMID: 11960423]J Am Chem Soc. 124 (2002) 4176-7
- Functional expression of genes involved in the biosynthesis of the novel polyketide chain extension unit, methoxymalonyl-acyl carrier protein, and engineered biosynthesis of 2-desmethyl-2-methoxy-6-deoxyerythronolide B.
- Kato Y, Bai L, Xue Q, Revill WP, Yu TW, Floss HG[PMID: 11996558]J Am Chem Soc. 124 (2002) 5268-9
- Identification of asm19 as an acyltransferase attaching the biologically essential ester side chain of ansamitocins using N-desmethyl-4,5-desepoxymaytansinol, not maytansinol, as its substrate.
- Moss SJ, Bai L, Toelzer S, Carroll BJ, Mahmud T, Yu TW, Floss HG[PMID: 12047169]J Am Chem Soc. 124 (2002) 6544-5
- The biosynthetic gene cluster of the maytansinoid antitumor agent ansamitocin from Actinosynnema pretiosum.
- Yu TW, Bai L, Clade D, Hoffmann D, Toelzer S, Trinh KQ, Xu J, Moss SJ, Leistner E, Floss HG[PMID: 12060743]Proc Natl Acad Sci U S A. 99 (2002) 7968-73
- The post-polyketide synthase modification steps in the biosynthesis of the antitumor agent ansamitocin by Actinosynnema pretiosum.
- Spiteller P, Bai L, Shang G, Carroll BJ, Yu TW, Floss HG[PMID: 14624546]J Am Chem Soc. 125 (2003) 14236-7
- Determination of the cryptic stereochemistry of the first PKS chain-extension step in ansamitocin biosynthesis by Actinosynnema pretiosum.
- Kubota T, Brunjes M, Frenzel T, Xu J, Kirschning A, Floss HG[PMID: 16927319]Chembiochem. 7 (2006) 1221-5
- On the biosynthetic origin of methoxymalonyl-acyl carrier protein, the substrate for incorporation of "glycolate" units into ansamitocin and soraphen A.
- Wenzel SC, Williamson RM, Grunanger C, Xu J, Gerth K, Martinez RA, Moss SJ, Carroll BJ, Grond S, Unkefer CJ, Muller R, Floss HG[PMID: 17076505]J Am Chem Soc. 128 (2006) 14325-36
- Amide N-glycosylation by Asm25, an N-glycosyltransferase of ansamitocins.
- Zhao P, Bai L, Ma J, Zeng Y, Li L, Zhang Y, Lu C, Dai H, Wu Z, Li Y, Wu X, Chen G, Hao X, Shen Y, Deng Z, Floss HG[PMID: 18721757]Chem Biol. 15 (2008) 863-74
- Timing of the Delta(10,12)-Delta(11,13) double bond migration during ansamitocin biosynthesis in Actinosynnema pretiosum.
- Taft F, Brunjes M, Knobloch T, Floss HG, Kirschning A[PMID: 19292483]J Am Chem Soc. 131 (2009) 3812-3
- Constitutive overexpression of asm2 and asm39 increases AP-3 production in the actinomycete Actinosynnema pretiosum.
- Ng D, Chin HK, Wong VV[PMID: 19609582]J Ind Microbiol Biotechnol. 36 (2009) 1345-51
- N-methylation of the amide bond by methyltransferase asm10 in ansamitocin biosynthesis.
- Wu Y, Kang Q, Shang G, Spiteller P, Carroll B, Yu TW, Su W, Bai L, Floss HG[PMID: 21681880]Chembiochem. 12 (2011) 1759-66
- Dual carbamoylations on the polyketide and glycosyl moiety by asm21 result in extended ansamitocin biosynthesis.
- Li Y, Zhao P, Kang Q, Ma J, Bai L, Deng Z[PMID: 22195559]Chem Biol. 18 (2011) 1571-80
- Asm8, a specific LAL-type activator of 3-amino-5-hydroxybenzoate biosynthesis in ansamitocin production.
- Pan W, Kang Q, Wang L, Bai L, Deng Z[PMID: 23832249]Sci China Life Sci. 56 (2013) 601-8
- Constitutive overexpression of asm18 increases the production and diversity of maytansinoids in Actinosynnema pretiosum.
- Li S, Lu C, Chang X, Shen Y[PMID: 26572523]Appl Microbiol Biotechnol. 100 (2016) 2641-9
Data download
History
- 2016-12-27[Update]
- 2013-09-04[Update]
- 2013-05-28[Release]