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

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

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
Abbreviations	D-KDO; KDO; dOclA
CAS number	10149-14-1, linear form
PubChem	445569
ChemSpider	106511^Y
ChEBI	CHEBI:32817^Y
Jmol-3D images	Image 1 Image 2
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
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
Properties
Molecular formula	C₈H₁₄O₈
Molar mass	238.19 g mol⁻¹
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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