| Revision as of 06:09, 11 December 2010 editحسن علي البط (talk | contribs)Extended confirmed users, Pending changes reviewers19,940 edits removed Category:Monosaccharides; added Category:Deoxy sugars using HotCat← Previous edit |
Latest revision as of 13:32, 6 May 2023 edit undoLegionMammal978 (talk | contribs)Extended confirmed users7,894 edits move semisystematic name |
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{{chembox |
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{{chembox |
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| verifiedrevid = 401736203 |
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| ImageFile = Perosamine.png |
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| ImageFile = Perosamine.png |
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| ImageSize = 200px |
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| ImageSize = 200px |
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| IUPACName = (2''S'',3''S'',4''R'',5''R'')-4-amino-2,3,5-trihydroxyhexanal |
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| IUPACName = 4-Amino-4,6-dideoxy-<small>D</small>-mannose |
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| SystematicName = (2''S'',3''S'',4''R'',5''R'')-4-Amino-2,3,5-trihydroxyhexanal |
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| OtherNames = 4-Amino-4,6-dideoxy-<small>D</small>-mannose |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 31348-80-8 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| PubChem = 161706 |
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| CASNo = 31348-80-8 |
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| SMILES = C((((C=O)O)O)N)O |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 73JD8O473G |
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| PubChem = 161706 |
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| SMILES = C((((C=O)O)O)N)O |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 142026 |
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| 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 |
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| InChIKey = UEHGPSGGFKLPTD-KVTDHHQDBX |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = UEHGPSGGFKLPTD-KVTDHHQDSA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>13</sub>NO<sub>4</sub> |
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| Formula = C<sub>6</sub>H<sub>13</sub>NO<sub>4</sub> |
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| MolarMass = 163.172 g/mol |
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| MolarMass = 163.172 g/mol |
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| Appearance = |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards = |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = |
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| AutoignitionPt = |
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'''Perosamine''' (or GDP-perosamine) is a ]-derived ] produced by some bacteria. |
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'''Perosamine''' (or '''GDP-perosamine''') is a ]-derived ] produced by some bacteria. |
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==Biological role== |
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==Biological role== |
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''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> |
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''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 |vauthors=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 |vauthors=Pawlak J, Sowiński P, Borowski E, Gariboldi P |title=Stereostructure of perimycin A |journal=J. Antibiot. |volume=48 |issue=9 |pages=1034–8 |date=September 1995 |pmid=7592049 |doi=10.7164/antibiotics.48.1034 |doi-access=free }}</ref> |
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==Biosynthesis== |
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==Biosynthesis== |
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Its biosynthesis from ] follows a pathway similar to that of ], but is different in that it is ] and does not undergo 3-OH deoxygenation or C-5 epimerization.<ref name="Albermann>{{cite journal |author=Albermann C, Piepersberg W |title=Expression and identification of the RfbE protein from Vibrio cholerae O1 and its use for the enzymatic synthesis of GDP-D-perosamine |journal=Glycobiology |volume=11 |issue=8 |pages=655–61 |year=2001 |month=August |pmid=11479276 |doi= |url=http://glycob.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=11479276 |accessdate=2010-01-24}}</ref> |
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Its biosynthesis from ] follows a pathway similar to that of ], but is different in that it is ] and does not undergo 3-OH deoxygenation or C-5 epimerization.<ref name="Albermann">{{cite journal |vauthors=Albermann C, Piepersberg W |title=Expression and identification of the RfbE protein from Vibrio cholerae O1 and its use for the enzymatic synthesis of GDP-D-perosamine |journal=Glycobiology |volume=11 |issue=8 |pages=655–61 |date=August 2001 |pmid=11479276 |doi= 10.1093/glycob/11.8.655|doi-access=free }}</ref> |
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===GDP-4-keto-6-deoxymannose-4-aminotransferase (GDP-perosamine synthase)=== |
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===GDP-4-keto-6-deoxymannose-4-aminotransferase (GDP-perosamine synthase)=== |
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GDP-perosamine synthase is a PLP-dependent ] that transfers a nitrogen from ] to the 4-keto position of GDP-4-keto-6-deoxymannose during the ] of GDP-perosamine.<ref name="Reeves"/> |
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GDP-perosamine synthase is a PLP-dependent ] that transfers a nitrogen from ] to the 4-keto position of GDP-4-keto-6-deoxymannose during the ] of GDP-perosamine.<ref name="Reeves"/> |
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