2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl methanethiosulfonate | 219668-45-8

• 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: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl methanethiosulfonate
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-methylsulfonylsulfanyloxan-2-yl]methyl acetate
• CAS: 219668-45-8
• 化学式: C₁₅H₂₂O₁₁S₂
• 分子量: 442.465
• InChiKey: IQLJSXWXOFAZAS-QMIVOQANSA-N

物化性质

• 熔点：
  148-151 °C
• 沸点：
  553.3±50.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  182
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl methanethiosulfonate 在 一溴化碘 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物
  参考文献：
  名称：

  糖基二硫化物：一类新的溶液和固相糖基供体

  摘要：

  混合糖基二硫化物不仅是糖模拟物，而且是糖基供体，可以很容易地以武装醚保护或解除武装酯保护的形式构建，并以相应的糖基甲硫代磺酸盐以可溶或固体支持的形式构建，并用于各种代表性受体的糖基化.

  DOI：

  10.1039/b008734n
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 氢溴酸 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 15.0h， 生成 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl methanethiosulfonate
  参考文献：
  名称：

  Glycosyl Disulfides:  Novel Glycosylating Reagents with Flexible Aglycon Alteration

  摘要：

  Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent-active reactivity tuning Strategies,.

  DOI：

  10.1021/jo051374j

文献信息

• A trisulfide-linked glycoprotein
  作者：Gonçalo J. L. Bernardes、Justin P. Marston、Andrei S. Batsanov、Judith A. K. Howard、Benjamin G. Davis

  DOI：10.1039/b706682a

  日期：——

  The first member of a novel class of chemoselective reagents, glycosyl methanedithiosulfonates, has been synthesized, identified and employed in the first examples of chemical, site-selective construction of a trisulfide-modified protein with complete conversion.

  我们合成、鉴定了一类新型化学选择性试剂--糖基甲二硫代磺酸酯，并将其用于化学、位点选择性构建三硫化修饰蛋白质并实现完全转化的首个实例中。
• 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。
• Elaboration of a novel type of interglycosidic linkage: syntheses of disulfide disaccharides
  作者：László Szilágyi、Tünde-Zita Illyés、Pál Herczegh

  DOI：10.1016/s0040-4039(01)00578-0

  日期：2001.6

  Asymmetric non-reducing disaccharides containing an interglycosidic disulfide linkage were synthesised under mild conditions through reaction of tetraacetyl-β-d-glucopyranosyl methanethiolsulfonate with O-acetylated 1-thio-aldopyranoses. The preferred conformation around the SS bond is close to that observed in unconstrained disulfides (−90°).

  通过使四乙酰基-β-d-吡喃葡萄糖基甲硫基磺酸盐与O-乙酰化的1-硫代-醛基吡喃糖反应，在温和条件下合成了具有糖苷间二硫键的不对称非还原性二糖。围绕SS键的优选构象与在无约束二硫键下（-90°）观察到的构象相近。
• 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。