Misplaced Pages

This is an old revision of this page, as edited by حسن علي البط (talk | contribs) at 06:09, 11 December 2010 (removed Category:Monosaccharides; added Category:Deoxy sugars using HotCat). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Perosamine

Names
IUPAC name (2S,3S,4R,5R)-4-amino-2,3,5-trihydroxyhexanal
Other names 4-Amino-4,6-dideoxy-D-mannose
Identifiers
CAS Number	31348-80-8
3D model (JSmol)	Interactive image
PubChem CID	161706
CompTox Dashboard (EPA)	DTXSID30185273
SMILES C((((C=O)O)O)N)O
Properties
Chemical formula	C6H13NO4
Molar mass	163.172 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

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 cholarae 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

1. ^ Samuel G, Reeves P (2003). "Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly". Carbohydr. Res. 338 (23): 2503–19. doi:10.1016/j.carres.2003.07.009. PMID 14670712.
2. Pawlak J, Sowiński P, Borowski E, Gariboldi P (1995). "Stereostructure of perimycin A". J. Antibiot. 48 (9): 1034–8. PMID 7592049. Retrieved 2010-01-24. {{cite journal}}: Unknown parameter |month= ignored (help)CS1 maint: multiple names: authors list (link)
3. Albermann C, Piepersberg W (2001). "Expression and identification of the RfbE protein from Vibrio cholerae O1 and its use for the enzymatic synthesis of GDP-D-perosamine". Glycobiology. 11 (8): 655–61. PMID 11479276. Retrieved 2010-01-24. {{cite journal}}: Unknown parameter |month= ignored (help)

This biochemistry article is a stub. You can help Misplaced Pages by expanding it.

• v
• t
• e

• Hexosamines
• Deoxy sugars
• Biochemistry stubs