Perosamine

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title: "Perosamine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["hexosamines", "deoxy-sugars"] topic_path: "general/hexosamines" source: "https://en.wikipedia.org/wiki/Perosamine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 401736203 | ImageFile = Perosamine.png | ImageSize = 200px | IUPACName = 4-Amino-4,6-dideoxy-D-mannose | SystematicName = (2S,3S,4R,5R)-4-Amino-2,3,5-trihydroxyhexanal | OtherNames = |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo = 31348-80-8 | UNII_Ref = | UNII = 73JD8O473G | PubChem = 161706 | SMILES = CC@HO | ChemSpiderID_Ref = | ChemSpiderID = 142026 | InChI = 1/C6H13NO4/c1-3(9)5(7)6(11)4(10)2-8/h2-6,9-11H,7H2,1H3/t3-,4-,5-,6-/m1/s1 | InChIKey = UEHGPSGGFKLPTD-KVTDHHQDBX | StdInChI_Ref = | StdInChI = 1S/C6H13NO4/c1-3(9)5(7)6(11)4(10)2-8/h2-6,9-11H,7H2,1H3/t3-,4-,5-,6-/m1/s1 | StdInChIKey_Ref = | StdInChIKey = UEHGPSGGFKLPTD-KVTDHHQDSA-N |Section2={{Chembox Properties | Formula = C6H13NO4 | MolarMass = 163.172 g/mol | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = Perosamine (or GDP-perosamine) is a mannose-derived 4-aminodeoxysugar produced by some bacteria.

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. The sugar is also found in perimycin, an antibiotic produced by the Gram-positive organism Streptomyces coelicolor var. aminophilus.

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.

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.

References

References

  1. (2003). "Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly". Carbohydr. Res..
  2. (September 1995). "Stereostructure of perimycin A". J. Antibiot..
  3. (August 2001). "Expression and identification of the RfbE protein from Vibrio cholerae O1 and its use for the enzymatic synthesis of GDP-D-perosamine". Glycobiology.

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hexosaminesdeoxy-sugars