2-(β-D-glucopyranosyl)ethyl methanethiosulfonate | 219668-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(β-D-glucopyranosyl)ethyl methanethiosulfonate
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(2-methylsulfonylsulfanylethoxy)oxane-3,4,5-triol
• CAS: 219668-52-7
• 化学式: C₉H₁₈O₈S₂
• 分子量: 318.369
• InChiKey: NUVZIEFUROVDGZ-SYHAXYEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  167
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-bromoethyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 2-(β-D-glucopyranosyl)ethyl methanethiosulfonate
  参考文献：
  名称：

  Controlled Site-Selective Glycosylation of Proteins by a Combined Site-Directed Mutagenesis and Chemical Modification Approach

  摘要：

  DOI：

  10.1021/jo9816461

文献信息

• 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
• Glycomethanethiosulfonates: powerful reagents for protein glycosylation
  作者：Benjamin G Davis、Michael A.T Maughan、Martin P Green、Astrid Ullman、J.Bryan Jones

  DOI：10.1016/s0957-4166(99)00497-8

  日期：2000.1

  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.