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MetaCyc Pathway: kanosamine biosynthesis I

Enzyme View:

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: Biosynthesis Secondary Metabolites Biosynthesis Sugar Derivatives Biosynthesis Kanosamine Biosynthesis

Some taxa known to possess this pathway include ? : Amycolatopsis mediterranei Inferred from experiment [Guo02c], Bacillus pumilus Inferred from experiment [Umezawa68]

Expected Taxonomic Range: Bacteria

Summary:
General Background

Kanosamine (3-amino-3-deoxy-D-glucose) is an antibiotic produced as an end product by Bacillus cereus [Milner96] and other bacteria [Fusetani87, Dolak80]. UDP-α-D-kanosamine is a proposed intermediate in kanamycin A biosynthesis in Streptomyces kanamyceticus [Kharel04] (see kanamycin biosynthesis). Kanosamine and UDP-α-D-kanosamine are also proposed intermediates in the biosynthesis of 3-amino-5-hydroxybenzoate (AHBA) [Arakawa02] (see pathway 3-amino-5-hydroxybenzoate biosynthesis) which is a precursor of the ansamycin and mitomycin classes of antibiotics (in [Yu01c]) (see pathway rifamycin B biosynthesis).

Early work using Bacillus pumilus (previously known as Bacillus aminoglucosidicus) provided experimental evidence for the biosynthesis of kanosamine via UDP-α-D-glucose, although the genes involved were not identified [Umezawa68]. Subsequent work using Amycolatopsis mediterranei provided further evidence for the UDP-α-D-glucose pathway (this pathway). It has also been proposed that the kab genes of Bacillus cereus are involved in kanosamine biosynthesis, although the pathway was not determined [Kevany09]. More recently, an alternate route for the biosynthesis of kanosamine has been described in Bacillus subtilis subtilis 168, in which kanosamine is derived from D-glucopyranose 6-phosphate rather than UDP-α-D-glucose [Vetter13] (see pathway kanosamine biosynthesis II).

About This Pathway

This is a proposed pathway for kanosamine biosynthesis in Amycolatopsis mediterranei [Guo02c, Arakawa02]. Evidence suggests that kanosamine is the source of the nitrogen atom in the 3-amino-5-hydroxybenzoate biosynthetic pathway (aminoshikimate pathway) [Guo02c, Arakawa02] as indicated in the pathway link. This is in contrast to the original proposal that the nitrogen atom was derived from transamination of D-erythrose 4-phosphate to 1-deoxy-1-imino-D-erythrose 4-phosphate by L-glutamine [Kim96i]. Preliminary studies using recombinant enzymes coexpressed in Escherichia coli suggested that the products of genes rifK and rifL may form a complex, jointly converting UDP-α-D-glucose to UDP-α-D-kanosamine through a UDP-3-dehydro-α-D-glucose intermediate (see comment listed as reference 25 in [Arakawa02]). These reactions produce NADH and use L-glutamine as a nitrogen source for kanosamine [Arakawa02]. The product of gene rifM has been predicted to encode a UDP-kanosamine phosphatase that catalyzes the conversion of UDP-α-D-kanosamine to kanosamine. This gene product and that of rifL have been shown to be essential for 3-amino-5-hydroxybenzoate biosynthesis [Yu01c]. Reviewed in [Floss11].

Superpathways: superpathway of rifamycin B biosynthesis

Variants: kanosamine biosynthesis II

Relationship Links: KEGG:PART-OF:rn01051

Credits:
Created 23-Jul-2008 by Fulcher CA , SRI International


References

Arakawa02: Arakawa K, Muller R, Mahmud T, Yu TW, Floss HG (2002). "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(36);10644-5. PMID: 12207505

Dolak80: Dolak LA, Castle TM, Dietz A, Laborde AL (1980). "3-Amino-3-deoxyglucose produced by a Streptomyces sp." J Antibiot (Tokyo) 33(8);900-1. PMID: 7429991

Floss05: Floss HG, Yu TW (2005). "Rifamycin-mode of action, resistance, and biosynthesis." Chem Rev 105(2);621-32. PMID: 15700959

Floss11: Floss HG, Yu TW, Arakawa K (2011). "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(1);35-44. PMID: 21081954

Fusetani87: Fusetani N, Ejima D, Matsunaga S, Hashimoto K, Itagaki K, Akagi Y, Taga N, Suzuki K (1987). "3-Amino-3-deoxy-D-glucose: an antibiotic produced by a deep-sea bacterium." Experientia 43(4);464-5. PMID: 3569498

Guo02c: Guo J, Frost JW (2002). "Kanosamine biosynthesis: a likely source of the aminoshikimate pathway's nitrogen atom." J Am Chem Soc 124(36);10642-3. PMID: 12207504

Kevany09: Kevany BM, Rasko DA, Thomas MG (2009). "Characterization of the complete zwittermicin A biosynthesis gene cluster from Bacillus cereus." Appl Environ Microbiol 75(4);1144-55. PMID: 19098220

Kharel04: Kharel MK, Subba B, Basnet DB, Woo JS, Lee HC, Liou K, Sohng JK (2004). "A gene cluster for biosynthesis of kanamycin from Streptomyces kanamyceticus: comparison with gentamicin biosynthetic gene cluster." Arch Biochem Biophys 429(2);204-14. PMID: 15313224

Kim96i: Kim C-G, Kirschning A, Bergon P, Zhou P, Su E, Sauerbrei B (1996). "Biosynthesis of 3-amino-5-hydroxybenzoic acid, the precursor of mC7N units in ansamycin antibiotics." J. Am. Chem. Soc. 118, 7486-7491.

Milner96: Milner JL, Silo-Suh L, Lee JC, He H, Clardy J, Handelsman J (1996). "Production of kanosamine by Bacillus cereus UW85." Appl Environ Microbiol 62(8);3061-5. PMID: 8702302

Umezawa68: Umezawa S, Shibahara S, Omoto S, Takeuchi T, Umezawa H (1968). "Studies on the biosynthesis of 3-amino-3-deoxy-D-glucose." J Antibiot (Tokyo) 21(8);485-91. PMID: 5708625

Vetter13: Vetter ND, Langill DM, Anjum S, Boisvert-Martel J, Jagdhane RC, Omene E, Zheng H, van Straaten KE, Asiamah I, Krol ES, Sanders DA, Palmer DR (2013). "A Previously Unrecognized Kanosamine Biosynthesis Pathway in Bacillus subtilis." J Am Chem Soc 135(16);5970-3. PMID: 23586652

Yu01c: Yu TW, Muller R, Muller M, Zhang X, Draeger G, Kim CG, Leistner E, Floss HG (2001). "Mutational analysis and reconstituted expression of the biosynthetic genes involved in the formation of 3-amino-5-hydroxybenzoic acid, the starter unit of rifamycin biosynthesis in amycolatopsis Mediterranei S699." J Biol Chem 276(16);12546-55. PMID: 11278540

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

August98: August PR, Tang L, Yoon YJ, Ning S, Muller R, Yu TW, Taylor M, Hoffmann D, Kim CG, Zhang X, Hutchinson CR, Floss HG (1998). "Biosynthesis of the ansamycin antibiotic rifamycin: deductions from the molecular analysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699." Chem Biol 5(2);69-79. PMID: 9512878

Eads99: Eads JC, Beeby M, Scapin G, Yu TW, Floss HG (1999). "Crystal structure of 3-amino-5-hydroxybenzoic acid (AHBA) synthase." Biochemistry 38(31);9840-9. PMID: 10433690

Kim98d: Kim CG, Yu TW, Fryhle CB, Handa S, Floss HG (1998). "3-Amino-5-hydroxybenzoic acid synthase, the terminal enzyme in the formation of the precursor of mC7N units in rifamycin and related antibiotics." J Biol Chem 273(11);6030-40. PMID: 9497318

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Lazarowski03: Lazarowski ER, Shea DA, Boucher RC, Harden TK (2003). "Release of cellular UDP-glucose as a potential extracellular signaling molecule." Mol Pharmacol 63(5);1190-7. PMID: 12695547

Schupp98: Schupp T, Toupet C, Engel N, Goff S (1998). "Cloning and sequence analysis of the putative rifamycin polyketide synthase gene cluster from Amycolatopsis mediterranei." FEMS Microbiol Lett 159(2);201-7. PMID: 9503613


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Sun Nov 23, 2014, biocyc14.