Glc(b1-3)GlcA | 10606-25-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Glc(b1-3)GlcA
• 英文别名: (2S,3S,4S,5R)-3,5,6-trihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• CAS: 10606-25-4
• 化学式: C₁₂H₂₀O₁₂
• 分子量: 356.284
• InChiKey: CRWRMHLBFCWZAT-SAZVSZAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  207
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 Glc(b1-3)GlcA 生成 Methyl 3-O-β-D-glucopyranosyl-D-glucopyranuronate
  参考文献：
  名称：

  Two synthetic antigens related to Streptococcus pneumoniae type 3 capsular polysaccharide

  摘要：

  The synthesis of the allyl beta-glycosides (8 and 20, respectively) of beta-D-GlcpA-(1----4)-D-Glcp and beta-D-Glcp-(1----3)-D-GlcpA (overlapping disaccharide fragments A and B) in the linear chain of the capsular polysaccharide (S3) from Streptococcus pneumoniae type 3 is described. Oxidation of allyl 2,3,6,2',3',4'-hexa-O-acetyl-beta-cellobioside with chromic acid and saponification of the product gave 8. The synthesis of 20 involved glycosylation of methyl 5-O-acetyl-1,2-O-isopropylidene-alpha-D-glucofuranuronate or its 3-O-trityl derivative and subsequent furanose----pyranose transformation. The derivatives 8 and 20 were each copolymerised with acrylamide. In serological tests (enzyme immunoassay and passive hemagglutination), the resulting antigens exhibited the specificity of S3. It was concluded that fragment A was a much stronger immunodeterminant than fragment B.

  DOI：

  10.1016/s0008-6215(00)90452-x
• 作为产物：
  描述：

  3,4,6-Tri-O-acetyl-1,2-O-<(1-exo-cyano)ethylidene>-α-D-glucopyranose 在 甲醇 、 sodium methylate 、 triphenylmethyl perchlorate 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 52.5h， 生成 Glc(b1-3)GlcA
  参考文献：
  名称：

  Two synthetic antigens related to Streptococcus pneumoniae type 3 capsular polysaccharide

  摘要：

  The synthesis of the allyl beta-glycosides (8 and 20, respectively) of beta-D-GlcpA-(1----4)-D-Glcp and beta-D-Glcp-(1----3)-D-GlcpA (overlapping disaccharide fragments A and B) in the linear chain of the capsular polysaccharide (S3) from Streptococcus pneumoniae type 3 is described. Oxidation of allyl 2,3,6,2',3',4'-hexa-O-acetyl-beta-cellobioside with chromic acid and saponification of the product gave 8. The synthesis of 20 involved glycosylation of methyl 5-O-acetyl-1,2-O-isopropylidene-alpha-D-glucofuranuronate or its 3-O-trityl derivative and subsequent furanose----pyranose transformation. The derivatives 8 and 20 were each copolymerised with acrylamide. In serological tests (enzyme immunoassay and passive hemagglutination), the resulting antigens exhibited the specificity of S3. It was concluded that fragment A was a much stronger immunodeterminant than fragment B.

  DOI：

  10.1016/s0008-6215(00)90452-x

文献信息

• Two synthetic antigens related to Streptococcus pneumoniae type 3 capsular polysaccharide
  作者：Anatoliy Ya. Chernyak、Konstantin V. Antonov、Nikolay K. Kochetkov、Leonid N. Padyukov、Nelly V. Tsvetkova

  DOI：10.1016/s0008-6215(00)90452-x

  日期：1985.9

  The synthesis of the allyl beta-glycosides (8 and 20, respectively) of beta-D-GlcpA-(1----4)-D-Glcp and beta-D-Glcp-(1----3)-D-GlcpA (overlapping disaccharide fragments A and B) in the linear chain of the capsular polysaccharide (S3) from Streptococcus pneumoniae type 3 is described. Oxidation of allyl 2,3,6,2',3',4'-hexa-O-acetyl-beta-cellobioside with chromic acid and saponification of the product gave 8. The synthesis of 20 involved glycosylation of methyl 5-O-acetyl-1,2-O-isopropylidene-alpha-D-glucofuranuronate or its 3-O-trityl derivative and subsequent furanose----pyranose transformation. The derivatives 8 and 20 were each copolymerised with acrylamide. In serological tests (enzyme immunoassay and passive hemagglutination), the resulting antigens exhibited the specificity of S3. It was concluded that fragment A was a much stronger immunodeterminant than fragment B.