close all open/close all
Jump cluster list

Cluster information : Ansamitocin


close this sectionCompound

Entry nameAnsamitocin
PKS TypeTypeI modular
Starter Unit3-amino-5-hydroxybenzoic acid (AHBA)
Chain Length8
Sugar Unitnone
ClassificationAnsamycin
ActivityAntifungal
Antitumor
CompositionP-3: C32H43ClN2O9
Ansamitocin

close this sectionOriginal source


close this sectionPKS/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
A35..434
PCP921..994
KS1020..1386
AT1535..1839
DH1879..2037
ER2298..2595
KR2605..2783
ACP2865..2935
KS2961..3335
AT3571..3873
DH3915..4077
KR4340..4510
ACP4577..4650
KS29..404
AT646..959
DH1004..1158
KR1410..1584
ACP1663..1735
KS1759..2131
AT2288..2571
ACP2916..2989
KS36..410
AT558..861
KR1143..1323
ACP1424..1494
KS34..408
AT557..862
DH907..1064
KR1321..1499
ACP1580..1650
KS1671..2031
AT2251..2553
dh2592..2732
KR2979..3154
ACP3242..3312

close this sectionReference

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

close this sectionData download

Compound nameGenomic
nucleotide
sequence
Nucleotide
sequences of the
coding regions
Translation of the
coding sequences
List of genes/ORFsGBK
Ansamitocin
Genomic nucleotide sequence
96 KB
Nucleotide sequences of the coding regions
26 KB
Translation of the coding sequences
17 KB
List of genes/ORFs
2 KB

 

 
GenBank format
190 KB
AF453501
Genomic nucleotide sequence
84 KB
Nucleotide sequences of the coding regions
81 KB
Translation of the coding sequences
29 KB
List of genes/ORFs
6 KB

 

 

 
U33059
Genomic nucleotide sequence
12 KB
Nucleotide sequences of the coding regions
11 KB
Translation of the coding sequences
4 KB
List of genes/ORFs
2 KB

 

 

 

close this sectionHistory

  • 2016-12-27[Update]
  • 2013-09-04[Update]
  • 2013-05-28[Release]