D-glycero-D-talo-oct-2-ulosonic acid | 498542-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-glycero-D-talo-oct-2-ulosonic acid
• 英文别名: D-glycero-alpha-D-talo-oct-2-ulopyranosonic acid；(2R,3S,4S,5R,6R)-6-[(1R)-1,2-dihydroxyethyl]-2,3,4,5-tetrahydroxyoxane-2-carboxylic acid
• CAS: 498542-43-1
• 化学式: C₈H₁₄O₉
• 分子量: 254.194
• InChiKey: GQQWVQCNFJXTNV-CXERMUKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  168
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 D-glycero-D-talo-oct-2-ulosonic acid 在 sodium tetrahydroborate 作用下， 生成 1,2,3,4,5,6,7,8-octa-O-methyl-D-erythro-L-allo-octitol 、 1,2,3,4,5,6,7,8-octa-O-methyl-D-erythro-L-altro-octitol
  参考文献：
  名称：

  Isolation and structural characterization of a (Kdo-isosteric) d-glycero-α-d-talo-oct-2-ulopyranosidonic acid (Ko) interlinking lipid A and core oligosaccharide in the lipopolysaccharide of Acinetobacter calcoaceticus NCTC 10305

  摘要：

  In Acinetobacter calcoaceticus NCTC 10305 and A. haemolyticus NCTC 10305 lipopolysaccharide (LPS) a Kdo (3-deoxy-D-manno-oct-2-ulosonic acid)-related octulosonic acid (Ko) interlinks the lipid A with the core-oligosaccharide. This Ko replaces the first Kdo (Kdo(I)) attached to the lipid A backbone in the LPS. The only structural difference between Kdo and Ko is the 3-hydroxylation. After the discovery of the final step in Ko-biosynthesis it is now generally accepted that Ko is structurally related to Kdo, although a final proof so far is lacking. In the present paper we describe the stereochemical determination of the natural Ko isolated from the LPS of A. calcoaceticus NCTC 10305 by chemical, mass spectrometry (MS), and H-1 and C-13 NMR spectroscopy. Our results show that in A. calcoaceticus D-glycero-alpha-D-talo-oct-2-ulopyranosonic acid (Dg alpha Dt-Kop) represents the Kdo-related sugar interlinking the core-oligosaccharide and the lipid A backbone. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.05.003