KEGG   PATHWAY: map01051Help
Entry
map01051                    Pathway                                

Name
Biosynthesis of ansamycins
Class
Metabolism; Metabolism of terpenoids and polyketides
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Pathway map
map01051  Biosynthesis of ansamycins
map01051

Ortholog table
Drug
D02549  Rifamycin (USAN/INN)
Reference
  Authors
Kang Q, Shen Y, Bai L
  Title
Biosynthesis of 3,5-AHBA-derived natural products.
  Journal
Nat Prod Rep 29:243-63 (2012)
DOI:10.1039/c2np00019a
Reference
  Authors
Floss HG, Yu TW, Arakawa K
  Title
The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), the precursor of mC7N units in ansamycin and mitomycin antibiotics: a review.
  Journal
J Antibiot (Tokyo) 64:35-44 (2011)
DOI:10.1038/ja.2010.139
Reference
  Authors
Guo J, Frost JW
  Title
Kanosamine biosynthesis: a likely source of the aminoshikimate pathway's nitrogen atom.
  Journal
J Am Chem Soc 124:10642-3 (2002)
DOI:10.1021/ja026628m
Reference
  Authors
Wenzel SC, Williamson RM, Grunanger C, Xu J, Gerth K, Martinez RA, Moss SJ, Carroll BJ, Grond S, Unkefer CJ, Muller R, Floss HG
  Title
On the biosynthetic origin of methoxymalonyl-acyl carrier protein, the substrate for incorporation of "glycolate" units into ansamitocin and soraphen A.
  Journal
J Am Chem Soc 128:14325-36 (2006)
DOI:10.1021/ja064408t
Reference
  Authors
Kato Y, Bai L, Xue Q, Revill WP, Yu TW, Floss HG
  Title
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.
  Journal
J Am Chem Soc 124:5268-9 (2002)
DOI:10.1021/ja0127483
Reference
  Authors
Yu TW, Bai L, Clade D, Hoffmann D, Toelzer S, Trinh KQ, Xu J, Moss SJ, Leistner E, Floss HG
  Title
The biosynthetic gene cluster of the maytansinoid antitumor agent ansamitocin from Actinosynnema pretiosum.
  Journal
Proc Natl Acad Sci U S A 99:7968-73 (2002)
DOI:10.1073/pnas.092697199
Reference
  Authors
Spiteller P, Bai L, Shang G, Carroll BJ, Yu TW, Floss HG
  Title
The post-polyketide synthase modification steps in the biosynthesis of the antitumor agent ansamitocin by Actinosynnema pretiosum.
  Journal
J Am Chem Soc 125:14236-7 (2003)
DOI:10.1021/ja038166y
Reference
  Authors
Taft F, Brunjes M, Knobloch T, Floss HG, Kirschning A
  Title
Timing of the Delta(10,12)-Delta(11,13) double bond migration during ansamitocin biosynthesis in Actinosynnema pretiosum.
  Journal
J Am Chem Soc 131:3812-3 (2009)
DOI:10.1021/ja8088923
Reference
  Authors
Li Y, Zhao P, Kang Q, Ma J, Bai L, Deng Z
  Title
Dual carbamoylations on the polyketide and glycosyl moiety by asm21 result in extended ansamitocin biosynthesis.
  Journal
Chem Biol 18:1571-80 (2011)
DOI:10.1016/j.chembiol.2011.11.007
Reference
  Authors
Wu Y, Kang Q, Shang G, Spiteller P, Carroll B, Yu TW, Su W, Bai L, Floss HG
  Title
N-methylation of the amide bond by methyltransferase asm10 in ansamitocin biosynthesis.
  Journal
Chembiochem 12:1759-66 (2011)
DOI:10.1002/cbic.201100062
Reference
  Authors
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
  Title
Amide N-glycosylation by Asm25, an N-glycosyltransferase of ansamitocins.
  Journal
Chem Biol 15:863-74 (2008)
DOI:10.1016/j.chembiol.2008.06.007
Reference
  Authors
Arakawa K, Muller R, Mahmud T, Yu TW, Floss HG
  Title
Characterization of the early stage aminoshikimate pathway in the formation of 3-amino-5-hydroxybenzoic acid: the RifN protein specifically converts kanosamine into kanosamine 6-phosphate.
  Journal
J Am Chem Soc 124:10644-5 (2002)
DOI:10.1021/ja0206339
Reference
  Authors
Watanabe K, Rude MA, Walsh CT, Khosla C
  Title
Engineered biosynthesis of an ansamycin polyketide precursor in Escherichia coli.
  Journal
Proc Natl Acad Sci U S A 100:9774-8 (2003)
DOI:10.1073/pnas.1632167100
Reference
  Authors
Floss HG, Yu TW.
  Title
Rifamycin-mode of action, resistance, and biosynthesis.
  Journal
Chem Rev 105:621-32 (2005)
DOI:10.1021/cr030112j
Reference
  Authors
Xu J, Mahmud T, Floss HG
  Title
Isolation and characterization of 27-O-demethylrifamycin SV methyltransferase provides new insights into the post-PKS modification steps during the biosynthesis of the antitubercular drug rifamycin B by Amycolatopsis mediterranei S699.
  Journal
Arch Biochem Biophys 411:277-88 (2003)
DOI:10.1016/S0003-9861(03)00004-3
Reference
  Authors
Xiong Y, Wu X, Mahmud T
  Title
A homologue of the Mycobacterium tuberculosis PapA5 protein, rif-orf20, is an acetyltransferase involved in the biosynthesis of antitubercular drug rifamycin B by Amycolatopsis mediterranei S699.
  Journal
Chembiochem 6:834-7 (2005)
DOI:10.1002/cbic.200400387
Reference
  Authors
Xu J, Wan E, Kim CJ, Floss HG, Mahmud T
  Title
Identification of tailoring genes involved in the modification of the polyketide backbone of rifamycin B by Amycolatopsis mediterranei S699.
  Journal
Microbiology 151:2515-28 (2005)
DOI:10.1099/mic.0.28138-0
KO pathway
ko01051   

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