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

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3-Deoxy-d-manno-oct-2-ulosonic acid
3-Deoxy-D-manno-oct-2-ulosonic acid linear.png
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)
AbbreviationsD-KDO; KDO; dOclA
ChEBI
ChemSpider
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: KYQCXUMVJGMDNG-SHUUEZRQSA-N Yes check.svgY
  • 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
  • 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
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
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 b-anomer. The chiral centers are indicated by asterisks. 3-Deoxy-D-manno-oct-2-ulosonic acid.svg
The cyclization of 3-deoxy-d-manno-oct-2-ulosonic acid to the β-anomer. The chiral centers are indicated by asterisks.

Related Research Articles

Sugar acid

A Sugar acid or acidic sugar is a monosaccharide with a carboxyl group at one end or both ends of its chain.

WAAA may refer to:

In enzymology, a 3-deoxyoctulosonase (EC 3.2.1.144) is an enzyme that catalyzes the chemical reaction

In enzymology, a 3-deoxy-8-phosphooctulonate synthase (EC 2.5.1.55) is an enzyme that catalyzes the chemical reaction

In enzymology, a 3-deoxy-manno-octulosonate cytidylyltransferase is an enzyme that catalyzes the chemical reaction

Saccharolipid

Saccharolipids are chemical compounds belonging to the general category of glycolipids. Their chemical structure involves fatty acids linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a monosaccharide substitutes for the glycerol backbone present in glycerolipids and glycerophospholipids. The most familiar saccharolipids are the acylated glucosamine precursors of the lipid A component of the lipopolysaccharides in Gram-negative bacteria. Typical lipid A molecules are disaccharides of glucosamine, which are derivatized with as many as seven fatty-acyl chains. The minimal lipopolysaccharide required for growth in Escherichia coli is Kdo2-Lipid A, a hexa-acylated disaccharide of glucosamine (LipidA) that is glycosylated with two 3-deoxy-D-manno-octulosonic acid (Kdo) residues.

Core oligosaccharide is a short chain of sugar residues within Gram-negative lipopolysaccharide (LPS). Core-OS are highly diverse among bacterial species and even within strains of species

Haloacid dehydrogenase superfamily

The haloacid dehydrogenase superfamily is a superfamily of enzymes that include phosphatases, phosphonatases, P-type ATPases, beta-phosphoglucomutases, phosphomannomutases, and dehalogenases, and are involved in a variety of cellular processes ranging from amino acid biosynthesis to detoxification.

In molecular biology, the lipopolysaccharide kinase (Kdo/WaaP) family is a family of kinases.

Lipid IVA 3-deoxy-D-manno-octulosonic acid transferase is an enzyme with systematic name CMP-3-deoxy-D-manno-oct-2-ulosonate:lipid IVA 3-deoxy-D-manno-oct-2-ulosonate transferase. This enzyme catalyses the following chemical reaction

KDO transferase may refer to:

WaaA (gene) may refer to:

KdtA may refer to:

3-deoxy-D-manno-oct-2-ulosonic acid transferase may refer to:

3-deoxy-manno-octulosonic acid transferase may refer to:

(KDO)-lipid IVA 3-deoxy-D-manno-octulosonic acid transferase is an enzyme with systematic name CMP-3-deoxy-D-manno-oct-2-ulosonate:(KDO)-lipid IVA 3-deoxy-D-manno-oct-2-ulosonate transferase. This enzyme catalyses the following chemical reaction

(KDO)2-lipid IVA (2-8) 3-deoxy-D-manno-octulosonic acid transferase is an enzyme with systematic name CMP-3-deoxy-D-manno-oct-2-ulosonate:(KDO)2-lipid IVA 3-deoxy-D-manno-oct-2-ulosonate transferase . This enzyme catalyses the following chemical reaction

(KDO)3-lipid IVA (2-4) 3-deoxy-D-manno-octulosonic acid transferase is an enzyme with systematic name CMP-3-deoxy-D-manno-oct-2-ulosonate:(KDO)3-lipid IVA 3-deoxy-D-manno-oct-2-ulosonate transferase . This enzyme catalyses the following chemical reaction

3-deoxy-D-manno-octulosonic acid kinase is an enzyme with systematic name ATP:(KDO)-lipid IVA 3-deoxy-alpha-D-manno-oct-2-ulopyranose 4-phosphotransferase. This enzyme catalyses the following chemical reaction

3-Deoxy-2-octulosonidase is an enzyme with systematic name capsular-polysaccharide 3-deoxy-D-manno-2-octulosonohydrolase. This enzyme catalyses the following chemical reaction

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.


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