2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)ethyl methanethiosulfonate | 219668-69-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)ethyl methanethiosulfonate
• 英文别名: [(2R,3R,4S,5S,6S)-3,4,5-triacetyloxy-6-(2-methylsulfonylsulfanylethoxy)oxan-2-yl]methyl acetate
• CAS: 219668-69-6
• 化学式: C₁₇H₂₆O₁₂S₂
• 分子量: 486.518
• InChiKey: WQWKTOLTNOIGLP-NRKLIOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  192
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)ethyl methanethiosulfonate 、 TREN-(SAc)2 在 sodium hydroxide 、 水 作用下， 以62%的产率得到
  参考文献：
  名称：

  WO2006/55437

  摘要：

  公开号：
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 在 三氟化硼乙醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)ethyl methanethiosulfonate
  参考文献：
  名称：

  Glycomethanethiosulfonates: powerful reagents for protein glycosylation

  摘要：

  Twelve novel glycomethanethiosulfonate (glyco-MTS) protein glycosylation reagents have been prepared. Their use in a controlled site-selective glycosylation strategy that combines site-directed mutagenesis with chemical modification allows protein glycosylation with concomitant control of (i) site, (ii) carbohydrate, (iii) anomeric stereochemistry, (iv) sugar to protein spacer arm nature and (v) degree of glycan protection. The ability of these highly selective and yet reactive reagents has been illustrated by the introduction of D-glucosyl and N-Ac-D-glucosaminyl residues to both external and hindered internal sites in a model protein - the serine protease enzyme subtilisin Bacillus lentus (SBL) - using corresponding gluco-MTS 1 and N-Ac-glucosamine-MTS 2. Molecular modelling studies provide a rationale for the strikingly different effects of these reagents on the properties of the protein despite differing only in the nature of their C-2 substituents. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00497-8

文献信息

• The controlled glycosylation of a protein with a bivalent glycan: towards a new class of glycoconjugates, glycodendriproteins
  作者：Benjamin G. Davis

  DOI：10.1039/b009184g

  日期：——

  The use of a novel bivalent carbohydrate modification reagent, based on a flexible, branched divalent core in a combined site-directed mutagenesis and chemical modification strategy has allowed the first controlled synthesis of a pure protein bearing a branched glycan or a first generation glycodendriprotein.

  在定点突变和化学修饰相结合的策略中，使用了一种新型的二价碳水化合物修饰试剂，该试剂以灵活的支化二价核心为基础，首次可控合成带有支化聚糖的纯蛋白质或第一代糖端三蛋白。
• Controlled Site-Selective Glycosylation of Proteins by a Combined Site-Directed Mutagenesis and Chemical Modification Approach
  作者：Benjamin G. Davis、Richard C. Lloyd、J. Bryan Jones

  DOI：10.1021/jo9816461

  日期：1998.12.1