1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside | 214468-40-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside
• CAS: 214468-40-3
• 化学式: C₂₅H₃₂O₅Si
• 分子量: 440.612
• InChiKey: VNCLNDVMZDFAGV-BMXMUORJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  49.45
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside 在 palladium on activated charcoal molecular sieve 、 氢气 、 zinc(II) chloride 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 23.5h， 生成 (2S,5R)-6-tert-Butoxycarbonylamino-5-[(3aS,4R,6R,7R,7aR)-4-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoic acid
  参考文献：
  名称：

  T Cells Recognize a Glycopeptide Derived from Type II Collagen in a Model for Rheumatoid Arthritis

  摘要：

  Even though most eucaryotic proteins are glycosylated, very Little is known on if, or how, the glycans influence essential immunological events such as antigen processing, major histocompatibility complex (MHC) restricted presentation, and recognition by T cells. We have used synthetic glycopeptides to elucidate the specificity of T cell hybridomas, obtained by immunization with the glycoprotein type II collagen in a mouse model for rheumatoid arthritis. To enable these studies, glycosylated and suitably protected derivatives of (5R)-5-hydroxy-L-lysine, and the similar 5-hydroxy-L-norvaline, were prepared and then used in Fmoc solid-phase synthesis of glycopeptides related to the immunodominant fragment from type II collagen, CII(256-270). Evaluation of the synthetic glycopeptides provided evidence that antigen-presenting cells can indeed process glycoproteins to glycopeptides, which elicit a T cell response when presented by class II MHC molecules. A glycopeptide carrying a single B-D-galactosyl residue attached to hydroxylysine at position 264 in the center of the CII(256-270) peptide was recognized by most of the hybridomas in a way involving specific contacts between the carbohydrate and the T cell receptor. The results suggest an explanation for the recent observation that glycosylated type II collagen induces more severe forms of arthritis in the mouse than deglycosylated type II collagen and provide additional knowledge on how rheumatoid arthritis may occur also in humans.

  DOI：

  10.1021/ja980489k
• 作为产物：
  描述：

  3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-D-galactal 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 1.0h， 生成 1,2-dihydro-6-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  酸不稳定的保护基团用于碳水化合物部分的合成与II型胶原有关的糖肽

  摘要：

  带有甲硅烷基，异亚丙基和4-甲氧基苄基保护基的β-D-半乳糖吡喃糖基和α-D-吡喃葡萄糖基-β-D-吡喃半乳糖基已连接到氨基酸5-羟基-L-正缬氨酸上。所得的糖基化结构单元用于与II型胶原蛋白片段相关的糖肽的Fmoc固相合成，该片段在类风湿性关节炎小鼠模型中具有免疫优势。在使O-糖苷键保持完整的条件下，在固相进行酸催化的糖肽裂解过程中，用于碳水化合物部分的保护基被完全除去。

  DOI：

  10.1016/s0040-4020(98)83057-3

文献信息

• Preparation of a Diglycosylated Hydroxylysine Building Block Used in Solid-Phase Synthesis of a Glycopeptide from Type II Collagen
  作者：Johan Broddefalk、Mattias Forsgren、Ingmar Sethson、Jan Kihlberg

  DOI：10.1021/jo990853d

  日期：1999.11.1