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

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.
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
3D model (JSmol)
Abbreviations D-KDO; KDO; dOclA
ChEBI
ChemSpider
UNII
Properties
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).
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Infobox references

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. PMID 4287911.


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