Perosamine

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;
ChemSpider	142026 ;
PubChem CID	161706;
UNII	73JD8O473G ;
CompTox Dashboard (EPA)	DTXSID30185273 ;
	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/s1 Key: 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/s1 Key: UEHGPSGGFKLPTD-KVTDHHQDBX;
	SMILES C[C@H]([C@H]([C@@H]([C@@H](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 [77 °F], 100 kPa).
	verify (what is ?)
	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 cholerae O1, E. coli O157:H7 and Caulobacter crescentus CB15.[1] The sugar is also found in perimycin, an antibiotic produced by the Gram-positive organism Streptomyces coelicolor var. aminophilus.[2]

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.[3]

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.[1]

gollark: <:rust:749384160065355869> <:rust:749384160065355869> <:rust:749384160065355869> <:rust:749384160065355869> <:rust:749384160065355869>

gollark: A programming language!

gollark: <:rust:749384160065355869>

gollark: It's the Rust mascot crab.

gollark: Well, I actually bifurcated the universe into two, one which has Discord's bot API allow arbitrary presence information and one where someone made the game "with numbers" in 2007.

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 (September 1995). "Stereostructure of perimycin A". J. Antibiot. 48 (9): 1034–8. doi:10.7164/antibiotics.48.1034. PMID 7592049. Retrieved 2010-01-24.
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. Retrieved 2010-01-24.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[Reeves-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.

[Pawlak-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. Retrieved 2010-01-24.

[Albermann-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. Retrieved 2010-01-24.