| Revision as of 17:16, 28 January 2010 editPdcook (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers35,959 edits servariant, gram positive← Previous edit | Revision as of 18:13, 28 January 2010 edit undoPdcook (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers35,959 edits chg to n acetylNext edit → | ||
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| ==Biological role== | ==Biological role== | ||
| ''N''-acetyl-perosamine is found in the ''O''-antigen of ] bacteria such as ] ''O''1, ] ''O''157:H7 and '']'' CB15.<ref name="Reeves">{{cite journal |author=Samuel G, Reeves P |title=Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly |journal=Carbohydr. Res. |volume=338 |issue=23 |pages=2503–19 |year=2003 |pmid=14670712 |doi=10.1016/j.carres.2003.07.009}}</ref> The sugar is also found in ], an ] produced by the ] organism ''] coelicolor'' var. aminophilus.<ref name="Pawlak">{{cite journal |author=Pawlak J, Sowiński P, Borowski E, Gariboldi P |title=Stereostructure of perimycin A |journal=J. Antibiot. |volume=48 |issue=9 |pages=1034–8 |year=1995 |month=September |pmid=7592049 |doi= |url=http://www.journalarchive.jst.go.jp/english/jnlabstract_en.php?cdjournal=antibiotics1968&cdvol=48&noissue=9&startpage=1034 |accessdate=2010-01-24}}</ref> | |||
| ==Biosynthesis== | ==Biosynthesis== | ||
Revision as of 18:13, 28 January 2010
| |
| 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 | |
| 3D model (JSmol) | |
| PubChem CID | |
| CompTox Dashboard (EPA) | |
SMILES
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| 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 a C-5 epimerization. The final enzyme in the pathway, GDP-D-perosamine synthase, is a PLP-dependent enzyme that transfers an amino group from glutamate to the C-4 position of the sugar.
References
- 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.
- 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) - 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)
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