KEGG   PATHWAY: rn01051Help
Entry
rn01051                     Pathway                                

Name
Biosynthesis of ansamycins
Class
Metabolism; Metabolism of terpenoids and polyketides
Pathway map
rn01051  Biosynthesis of ansamycins
rn01051

Ortholog table
Reaction
R06586  UDP-3-ketoglucose:L-glutamate aminotransferase
R06587   
R06588  ATP:kanosamine 6-phosphotransferase
R06589   
R06590  sedoheptulose-7-phosphate:D-glyceraldehyde-3-phosphate glycolaldehydetransferase
R06591  phosphoenolpyruvate:imino-D-erythrose-4-phosphate C-(1-carboxyvinyl)transferase (phosphate hydrolysing, 2-carboxy-2-oxoethyl-forming)
R06592   
R06593   
R06594  UDP-glucose:NAD+ 3-oxidoreductase
R06595  5-amino-5-deoxy-3-dehydroshikimate hydro-lyase (3-amino-5-hydroxybenzoate-forming)
R06597   
R06599   
R06600   
R06991   
R06992   
R06993   
R06994   
R06995   
R06996   
R06997   
R06998  S-adenosyl-L-methionine:27-O-demethylrifamycin-SV 27-O-methyltransferase
R06999   
R09851   
R09852   
R09853  carbamoyl-phosphate:20-O-methyl-19-chloroproansamitocin carbamoyltransferase
R09854   
R09855   
R09856  S-adenosyl-L-methionine:N-demethylansamitocin-P-3 N-methyltransferase
R09857  UDP-glucose:N-demethylansamitocin-P-3 beta-D-glucosyltransferase
R09858  carbamoyl-phosphate:ansamitocinoside-P-3 carbamoyltransferase
Compound
C00029  UDP-glucose
C01848  Rifamycin B
C12044  Rifamycin
C12045  Ansamitocin P-3
C12106  AminoDAHP
C12107  3-Amino-5-hydroxybenzoate
C12108  5-Amino-5-deoxy-3-dehydroshikimate
C12109  AminoDHQ
C12176  Proansamycin X
C12177  Proansamitocin
C12210  UDP-3-ketoglucose
C12211  UDP-kanosamine
C12212  Kanosamine
C12213  Kanosamine 6-phosphate
C12214  Aminofructose 6-phosphate
C12215  Iminoerythrose 4-phosphate
C12246  Protorifamycin I
C12247  Rifamycin W
C14540  Rifamycin S
C14721  34a-Deoxy-rifamycin W
C14722  Rifamycin W-hemiacetal
C14723  Rifamycin Z
C14724  Demethyl-desacetyl-rifamycin S
C14725  27-O-Demethyl-25-O-desacetylrifamycin SV
C14727  27-O-Demethylrifamycin SV
C20134  19-Chloroproansamitocin
C20135  20-O-Methyl-19-chloroproansamitocin
C20136  N-Demethyl-desepoxymaytansinol
C20137  N-Demethyl-desepoxyansamitocin P-3
C20138  N-Demethylansamitocin P-3
C20139  Ansamitocinoside P-3
C20140  4''-O-Carbamoyl ansamitocinoside P-3
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
Related
pathway
rn00520  Amino sugar and nucleotide sugar metabolism
KO pathway
ko01051   

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