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) Y
3D model (JSmol)	Interactive image Interactive image
Abbreviations	D-KDO; KDO; dOclA
ChEBI	CHEBI:32817  Y
ChemSpider	106511  Y
PubChem CID	445569
UNII	ZWK96OG89F  (linear form) Y
CompTox Dashboard (EPA)	DTXSID501265068
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 Y Key: KYQCXUMVJGMDNG-SHUUEZRQSA-N Y 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	238.192 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

3-Deoxy-d-manno-oct-2-ulosonic acid (ketodeoxyoctonic acid; KDO; IUPAC symbol 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

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. doi: 10.1016/S0021-9258(18)96516-6 . PMID   4287911.