Biosynthesis of ansamycins

Metabolism; Metabolism of terpenoids and polyketides

PMID:22193711

Kang Q, Shen Y, Bai L

Biosynthesis of 3,5-AHBA-derived natural products.

Nat Prod Rep 29:243-63 (2012)

PMID:21081954

Floss HG, Yu TW, Arakawa K

The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), the precursor of mC7N units in ansamycin and mitomycin antibiotics: a review.

J Antibiot (Tokyo) 64:35-44 (2011)

PMID:12207504

Guo J, Frost JW

Kanosamine biosynthesis: a likely source of the aminoshikimate pathway's nitrogen atom.

J Am Chem Soc 124:10642-3 (2002)

PMID:17076505

Wenzel SC, Williamson RM, Grunanger C, Xu J, Gerth K, Martinez RA, Moss SJ, Carroll BJ, Grond S, Unkefer CJ, Muller R, Floss HG

On the biosynthetic origin of methoxymalonyl-acyl carrier protein, the substrate  for incorporation of "glycolate" units into ansamitocin and soraphen A.

J Am Chem Soc 128:14325-36 (2006)

PMID:11996558

Kato Y, Bai L, Xue Q, Revill WP, Yu TW, Floss HG

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.

J Am Chem Soc 124:5268-9 (2002)

PMID:12060743

Yu TW, Bai L, Clade D, Hoffmann D, Toelzer S, Trinh KQ, Xu J, Moss SJ, Leistner E, Floss HG

The biosynthetic gene cluster of the maytansinoid antitumor agent ansamitocin from Actinosynnema pretiosum.

Proc Natl Acad Sci U S A 99:7968-73 (2002)

PMID:14624546

Spiteller P, Bai L, Shang G, Carroll BJ, Yu TW, Floss HG

The post-polyketide synthase modification steps in the biosynthesis of the antitumor agent ansamitocin by Actinosynnema pretiosum.

J Am Chem Soc 125:14236-7 (2003)

PMID:19292483

Taft F, Brunjes M, Knobloch T, Floss HG, Kirschning A

Timing of the Delta(10,12)-Delta(11,13) double bond migration during ansamitocin  biosynthesis in Actinosynnema pretiosum.

J Am Chem Soc 131:3812-3 (2009)

PMID:22195559

Li Y, Zhao P, Kang Q, Ma J, Bai L, Deng Z

Dual carbamoylations on the polyketide and glycosyl moiety by asm21 result in extended ansamitocin biosynthesis.

Chem Biol 18:1571-80 (2011)

PMID:21681880

Wu Y, Kang Q, Shang G, Spiteller P, Carroll B, Yu TW, Su W, Bai L, Floss HG

N-methylation of the amide bond by methyltransferase asm10 in ansamitocin biosynthesis.

Chembiochem 12:1759-66 (2011)

PMID:18721757

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

Amide N-glycosylation by Asm25, an N-glycosyltransferase of ansamitocins.

Chem Biol 15:863-74 (2008)

PMID:12207505

Arakawa K, Muller R, Mahmud T, Yu TW, Floss HG

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.

J Am Chem Soc 124:10644-5 (2002)

PMID:12888623

Watanabe K, Rude MA, Walsh CT, Khosla C

Engineered biosynthesis of an ansamycin polyketide precursor in Escherichia coli.

Proc Natl Acad Sci U S A 100:9774-8 (2003)

PMID:15700959

Floss HG, Yu TW.

Rifamycin-mode of action, resistance, and biosynthesis.

Chem Rev 105:621-32 (2005)

PMID:12623077

Xu J, Mahmud T, Floss HG

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.

Arch Biochem Biophys 411:277-88 (2003)

PMID:15791687

Xiong Y, Wu X, Mahmud T

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.

Chembiochem 6:834-7 (2005)

PMID:16079331

Xu J, Wan E, Kim CJ, Floss HG, Mahmud T

Identification of tailoring genes involved in the modification of the polyketide  backbone of rifamycin B by Amycolatopsis mediterranei S699.

Microbiology 151:2515-28 (2005)