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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 401736203
| ImageFile = Perosamine.png | ImageFile = Perosamine.png
| ImageSize = 200px | ImageSize = 200px
| IUPACName = (2''S'',3''S'',4''R'',5''R'')-4-amino-2,3,5-trihydroxyhexanal | IUPACName = 4-Amino-4,6-dideoxy-<small>D</small>-mannose
| SystematicName = (2''S'',3''S'',4''R'',5''R'')-4-Amino-2,3,5-trihydroxyhexanal
| OtherNames = 4-Amino-4,6-dideoxy-<small>D</small>-mannose
| OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
⚫ | CASNo = 31348-80-8
| CASNo_Ref = {{cascite|correct|??}}
⚫ | PubChem = 161706
⚫ | CASNo = 31348-80-8
⚫ | SMILES = C((((C=O)O)O)N)O
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 73JD8O473G
⚫ | PubChem = 161706
⚫ | SMILES = C((((C=O)O)O)N)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| 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 = {{stdinchicite|changed|chemspider}}
| 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 = {{stdinchicite|changed|chemspider}}
| StdInChIKey = UEHGPSGGFKLPTD-KVTDHHQDSA-N
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>13</sub>NO<sub>4</sub> | Formula = C<sub>6</sub>H<sub>13</sub>NO<sub>4</sub>
| MolarMass = 163.172 g/mol | MolarMass = 163.172 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}
'''Perosamine''' (or GDP-perosamine) is a ]-derived ] produced by some bacteria. '''Perosamine''' (or '''GDP-perosamine''') is a ]-derived ] produced by some bacteria.


==Biological role== ==Biological role==
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 ''] coelicolor''.<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> ''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>


==Biosynthesis== ==Biosynthesis==
Its biosynthesis from ] follows a pathway similar to that of ], but is different in that it is ] and does not undergo a 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> The final enzyme in the pathway, ], is a ]-dependent enzyme that transfers an amino group from glutamate to the C-4 position of the sugar. 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>
===GDP-4-keto-6-deoxymannose-4-aminotransferase (GDP-perosamine synthase)===
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"/>


== References == == References ==
{{Reflist}} {{Reflist}}


] ]
] ]

{{biochem-stub}}

Latest revision as of 13:32, 6 May 2023

Perosamine
Names
IUPAC name 4-Amino-4,6-dideoxy-D-mannose
Systematic IUPAC name (2S,3S,4R,5R)-4-Amino-2,3,5-trihydroxyhexanal
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H13NO4/c1-3(9)5(7)6(11)4(10)2-8/h2-6,9-11H,7H2,1H3/t3-,4-,5-,6-/m1/s1Key: UEHGPSGGFKLPTD-KVTDHHQDSA-N
  • 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/s1Key: UEHGPSGGFKLPTD-KVTDHHQDBX
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). ☒N verify (what is  ?) Infobox references
Chemical compound

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

  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 (September 1995). "Stereostructure of perimycin A". J. Antibiot. 48 (9): 1034–8. doi:10.7164/antibiotics.48.1034. PMID 7592049.
  3. Albermann C, Piepersberg W (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. 11 (8): 655–61. doi:10.1093/glycob/11.8.655. PMID 11479276.
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