Perosamine (or GDP-perosamine) is a mannose-derived 4-aminodeoxysugar produced by some bacteria.
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IUPAC name
4-Amino-4,6-dideoxy-D-mannose
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Systematic IUPAC name
(2S,3S,4R,5R)-4-Amino-2,3,5-trihydroxyhexanal | |
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3D model (JSmol)
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ChemSpider |
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PubChem CID
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UNII |
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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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Infobox references
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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]
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-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]