Perosamine
Chemical compound
From Wikipedia, the free encyclopedia
Perosamine (or GDP-perosamine) is a mannose-derived 4-aminodeoxysugar produced by some bacteria.
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| Names | |
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| IUPAC name
4-Amino-4,6-dideoxy-D-mannose | |
| Systematic IUPAC name
(2S,3S,4R,5R)-4-Amino-2,3,5-trihydroxyhexanal | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C6H13NO4 | |
| Molar mass | 163.172 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Biological role
N-acetyl-perosamine is found in the O-antigen of Gram-negative bacteria such as Vibrio cholerae O1, E. coli O157:H7 and Caulobacter crescentus CB15.[1] The sugar is also found in perimycin, an antibiotic produced by the Gram-positive organism Streptomyces coelicolor var. aminophilus.[2]
Biosynthesis
Its biosynthesis from mannose-1-phosphate follows a pathway similar to that of colitose, but is different in that it is aminated and does not undergo 3-OH deoxygenation or C-5 epimerization.[3]
GDP-4-keto-6-deoxymannose-4-aminotransferase (GDP-perosamine synthase)
GDP-perosamine synthase is a PLP-dependent enzyme that transfers a nitrogen from glutamate to the 4-keto position of GDP-4-keto-6-deoxymannose during the biosynthesis of GDP-perosamine.[1]