2-bromoethyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside | 152014-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromoethyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside
• 英文别名: 2-bromoethyl 4-O-beta-D-galactopyranosyl-beta-D-glucopyranoside；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6R)-6-(2-bromoethoxy)-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 152014-04-5
• 化学式: C₁₄H₂₅BrO₁₁
• 分子量: 449.25
• InChiKey: GVRORIVXGHKHBZ-VNQPAINQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-bromoethyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside 在 吡啶 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 6.67h， 生成 2-Bromoethyl 2,3,6-tri-O-benzoyl-4-O-(2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  The p-methoxybenzyl ether as an in situ-removable carbohydrate-protecting group: a simple one-pot synthesis of the globotetraose tetrasaccharide

  摘要：

  报告了一种一锅合成球四糖的四糖的方法。该合成方法依赖于使用对甲氧基苄醚作为原位可去除的保护基。N-碘代苏氨酸酯/三氟甲磺酸促进的糖苷化反应在-45 °C下，将2-溴乙基-2,3,6-三-O-苯甲酰基-4-O-(2,3,6-三-O-苯甲酰基-β-D-半乳糖吡喃糖) 5与苯基2,4,6-三-O-苯甲酰基-3-O-(4-甲氧基苄基)-1-硫代-β-D-半乳糖吡喃糖 6反应得到中间三糖体，随后通过将反应温度升高到0 °C反应40分钟去除对甲氧基苄醚。再次降低温度至-45 °C，然后添加甲基3,4,6-三-O-乙酰基-2-三氯乙氧基羰基氨基-2-脱氧-1-硫代-β-D-半乳糖吡喃糖 8，最终在一锅中以76%的优异产率获得球四糖四糖 11。

  DOI：

  10.1039/b009448j
• 作为产物：
  描述：

  1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-bromoethyl 4-O-β-D-galactopyranosyl-β-D-glucopyranoside
  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

• CHEMICALLY MODIFIED PROTEINS WITH A CARBOHYDRATE MOIETY
  申请人：——

  公开号：US20010018200A1

  公开（公告）日：2001-08-30

  The present invention relates to a chemically modified mutant protein including a cysteine residue substituted for a residue other than cysteine in a precursor protein, the substituted cysteine residue being subsequently modified by reacting the cysteine residue with a glycosylated thiosulfonate. Also, a method of producing the chemically modified mutant protein is provided. The present invention also relates to a glycosylated methanethiosulfonate. Another aspect of the present invention is a method of modifying the functional characteristics of a protein including providing a protein and reacting the protein with a glycosylated methanethiosulfonate reagent under conditions effective to produce a glycoprotein with altered functional characteristics as compared to the protein. In addition, the present invention relates to methods of determining the structure-function relationships of chemically modified mutant proteins.

  本发明涉及一种化学修饰的突变蛋白，包括在前体蛋白中用半胱氨酸残基替换非半胱氨酸残基，然后通过将半胱氨酸残基与糖基化硫代磺酸盐反应来修饰替换的半胱氨酸残基。此外，本发明还提供了一种制备化学修饰的突变蛋白的方法。本发明还涉及一种糖基化的甲硫代磺酸盐。本发明的另一方面是一种修改蛋白质功能特性的方法，包括提供蛋白质并将蛋白质与糖基化的甲硫代磺酸盐试剂反应，在有效条件下产生与蛋白质相比具有改变功能特性的糖蛋白。此外，本发明还涉及确定化学修饰的突变蛋白的结构-功能关系的方法。
• Chemically modified proteins with a carbohydrate moiety
  申请人：——

  公开号：US20020146803A1

  公开（公告）日：2002-10-10

  The present invention relates to a chemically modified mutant protein including a cysteine residue substituted for a residue other than cysteine in a precursor protein, the substituted cysteine residue being subsequently modified by reacting the cysteine residue with a glycosylated thiosulfonate. Also, a method of producing the chemically modified mutant protein is provided. The present invention also relates to a glycosylated methanethiosulfonate. Another aspect of the present invention is a method of modifying the functional characteristics of a protein including providing a protein and reacting the protein with a glycosylated methanethiosulfonate reagent under conditions effective to produce a glycoprotein with altered functional characteristics as compared to the protein. In addition, the present invention relates to methods of determining the structure-function relationships of chemically modified mutant proteins.

  本发明涉及一种化学修饰的突变蛋白，其包括在前体蛋白中以半胱氨酸取代其他氨基酸残基的半胱氨酸残基，随后通过将半胱氨酸残基与糖基化硫代磺酸盐反应来修饰替代的半胱氨酸残基。此外，本发明还提供了一种制备化学修饰的突变蛋白的方法。本发明还涉及一种糖基化甲硫磺酸盐。本发明的另一个方面是一种改变蛋白质功能特性的方法，包括提供蛋白质并在有效条件下将蛋白质与糖基化甲硫磺酸盐试剂反应，以产生与蛋白质相比具有改变的功能特性的糖基化蛋白质。此外，本发明还涉及确定化学修饰突变蛋白的结构-功能关系的方法。
• 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
• PEPTIDE-CARBOHYDRATE CONJUGATES GENERATING T-CELL IMMUNITY
  申请人：AstraZeneca AB

  公开号：EP0675733B1

  公开（公告）日：2000-12-06
• EP1093459A4
  申请人：——

  公开号：EP1093459A4

  公开（公告）日：2002-02-06