3-Deoxy-D-manno-oct-2-ulosonic acid

3-Deoxy-D-*manno*-oct-2-ulosonic acid
Names
	IUPAC name (4R,5R,6R,7R)-4,5,6,7,8-pentahydroxy-2-oxooctanoic acid
	Other names 2-Oxo-3-deoxy-D-mannooctonic acid; 2-Keto-3-Deoxy-D-manno-octonate; 2-Keto-3-deoxy-D-mannooctanoic acid; 3-Deoxy-D-manno-2-octulosonic acid; 3-Deoxy-D-manno-octulosonic acid
Identifiers
CAS Number	10149-14-1 linear form ;
3D model (JSmol)	Interactive image; Interactive image;
Abbreviations	D-KDO; KDO; dOclA
ChEBI	CHEBI:32817 ;
ChemSpider	106511 ;
PubChem CID	445569;
	InChI InChI=1S/C8H14O8/c9-2-5(12)7(14)6(13)3(10)1-4(11)8(15)16/h3,5-7,9-10,12-14H,1-2H2,(H,15,16)/t3-,5-,6-,7-/m1/s1 Key: KYQCXUMVJGMDNG-SHUUEZRQSA-N ; InChI=1/C8H14O8/c9-2-5(12)7(14)6(13)3(10)1-4(11)8(15)16/h3,5-7,9-10,12-14H,1-2H2,(H,15,16)/t3-,5-,6-,7-/m1/s1 Key: KYQCXUMVJGMDNG-SHUUEZRQBC;
	SMILES O[C@@H]([C@@H]([C@@H](CC(C(O)=O)=O)O)O)[C@H](O)CO; O=C(O)C(=O)C[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO;
Properties
Chemical formula	C8H14O8
Molar mass	238.19 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

3-Deoxy-D-manno-oct-2-ulosonic acid or keto-deoxyoctulosonate (KDO) is an ulosonic acid of a 2-ketooctose which is used by bacteria in the synthesis of lipopolysaccharides.^[1] The D-manno prefix indicates that the four chiral centers have the same configuration as D-mannose.

The cyclization of 3-deoxy-D-manno-oct-2-ulosonic acid to the β-anomer. The chiral centers are indicated by asterisks.

References

↑ Ghalambor, Mohammad Ali; Levine, Edward M.; Heath, Edward C. (1966). "The biosynthesis of cell wall lipopolysaccharide in Escherichia coli. III. The isolation and characterization of 3-deoxyoctulosonic acid". Journal of Biological Chemistry. 241 (13): 3207–15. PMID 4287911.

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[1] Ghalambor, Mohammad Ali; Levine, Edward M.; Heath, Edward C. (1966). "The biosynthesis of cell wall lipopolysaccharide in Escherichia coli. III. The isolation and characterization of 3-deoxyoctulosonic acid". Journal of Biological Chemistry. 241 (13): 3207–15. PMID 4287911.