10149-14-1

Basic information

• Product Name: (4R,5R,6R,7R)-2-Oxo-4,5,6,7,8-pentahydroxyoctanoic acid
• Synonyms: (4R,5R,6R,7R)-2-Oxo-4,5,6,7,8-pentahydroxyoctanoic acid;2-Oxo-3-deoxy-D-mannooctonic acid;3-Deoxy-D-manno-2-octulosonic acid;3-Deoxy-D-manno-octulosonic acid;keto-3-deoxy-D-manno-octulosonic acid;3-deoxy-D-manno-octulosonic acid (KDO)
• CAS NO: 10149-14-1
• Molecular Formula: C₈H₁₄O₈
• Molecular Weight: 238.192
• Mol File: 10149-14-1.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 621.7°Cat760mmHg
• Flash Point: 343.8°C
• Appearance: /
• Density: 1.684g/cm³
• Vapor Pressure: 4.64E-18mmHg at 25°C
• Refractive Index: 1.597
• CAS DataBase Reference: (4R,5R,6R,7R)-2-Oxo-4,5,6,7,8-pentahydroxyoctanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5R,6R,7R)-2-Oxo-4,5,6,7,8-pentahydroxyoctanoic acid(10149-14-1)
• EPA Substance Registry System: (4R,5R,6R,7R)-2-Oxo-4,5,6,7,8-pentahydroxyoctanoic acid(10149-14-1)

Safety Data

• Hazardous Substances Data: 10149-14-1(Hazardous Substances Data)

Usage

Description

3-Deoxy-D-manno-oct-2-ulosonic acid or KDO is an ulosonic acid of a 2-keto octose which is used by bacteria in the synthesis of lipo poly saccharides. The D-manno prefix indicates that four chiral centers have the same configuration as D-mannose.

InChI: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

Relevant articles and documents

Structural diversity of Burkholderia pseudomallei lipopolysaccharides affects innate immune signaling

Burkholderia pseudomallei (Bp) causes the disease melioidosis. The main cause of mortality in this disease is septic shock triggered by the host responding to lipopolysaccharide (LPS) components of the Gram-negative outer membrane. Bp LPS is thought to be a weak inducer of the host immune system. LPS from several strains of Bp were purified and their ability to induce the inflammatory mediators TNF-α and iNOS in murine macrophages at low concentrations was investigated. Innate and adaptive immunity qPCR arrays were used to profile expression patterns of 84 gene targets in response to the different LPS types. Additional qPCR validation confirmed large differences in macrophage response. LPS from a high-virulence serotype B strain 576a and a virulent rough central nervous system tropic strain MSHR435 greatly induced the innate immune response indicating that the immunopathogenesis of these strains is different than in infections with strains similar to the prototype strain 1026b. The accumulation of autophagic vesicles was also increased in macrophages challenged with highly immunogenic Bp LPS. Gene induction and concomitant cytokine secretion profiles of human PBMCs in response to the various LPS were also investigated. MALDI-TOF/TOF was used to probe the lipid A portions of the LPS, indicating substantial structural differences that likely play a role in host response to LPS. These findings add to the evolving knowledge of host-response to bacterial LPS, which can be used to better understand septic shock in melioidosis patients and in the rational design of vaccines.