S-α-D-glucopyranosyl-L-cysteine

• 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: S-α-D-glucopyranosyl-L-cysteine
• 英文别名: (2R)-2-amino-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanylpropanoic acid
• 化学式: C₉H₁₇NO₇S
• 分子量: 283.302
• InChiKey: WWUVPKJYNTWYIZ-AVLLYLPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  179
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-硫代-beta-D-葡萄糖五乙酸酯 在 盐酸 、 sodium methylate 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 生成 S-α-D-glucopyranosyl-L-cysteine
  参考文献：
  名称：

  Synthesis of S-Linked Glycosyl Amino Acids in Aqueous Solution with Unprotected Carbohydrates

  摘要：

  [GRAPHICS]The cyclic sulfamidate 5 was synthesized in 60% overall yield from L-serine benzyl ester, Compound 5 reacted cleanly with the sodium thiolate salt of a variety of unprotected 1-thio sugars in aqueous buffer to afford the corresponding S-linked amino acid glycoconjugates in good yields after hydrolysis of the N-sulfates.

  DOI：

  10.1021/ol006908b

文献信息

• Application of Serine- and Threonine-Derived Cyclic Sulfamidates for the Preparation of <i>S</i>-Linked Glycosyl Amino Acids in Solution- and Solid-Phase Peptide Synthesis
  作者：Scott B. Cohen、Randall L. Halcomb

  DOI：10.1021/ja011932l

  日期：2002.3.1

  Cyclic sulfamidates were synthesized in 60% yield from L-serine and allo-L-threonine, respectively. These sulfamidates reacted with a variety of unprotected 1-thio sugars in aqueous bicarbonate buffer (pH 8) to afford the corresponding S-linked serine- and threonine-glycosyl amino acids with good diastereo-selectivity (greater than or equal to97%) after hydrolysis of the A sulfates. The serine-derived sulfamidate was incorporated into a simple dlipeptide to generate a reactive dipeptide substrate that underwent chemoselective ligation with a 1-thio sugar to afford an S-linked glycopeptide. This sulfamidate was also incorporated into a peptide on a solid support in conjunction with solid-phase peptide synthesis. Chemoselective ligation of a 1-thio sugar with the cyclic sulfamidate was achieved on the solid support, followed by removal of the N-sulfate. Finally, the peptide chain of the resulting support-bound S-linked glycopeptide was extended using standard peptide synthesis procedures.
• Synthesis ofS-α-D-GlucosylatedL-Cysteine – A NovelS-Glycosyl Amino Acid
  作者：Ludwig Käsbeck、Horst Kessler

  DOI：10.1002/jlac.199719970123

  日期：1997.1

  AbstractWhereas S‐β‐D‐glucosylated L‐cysteine is easily available, the corresponding α‐anomer has not been prepared before. In this paper a solution to the synthetic problem is presented. The glycosylation of highly nucleophilic N‐phthaloyl‐L‐cysteine esters 4 and 5 with 2,3,4,6‐tetra‐O‐benzyl‐α‐L‐glucopyranosyl trichloroacetimidate in the presence of 1 equivalent of BF3 · Et2O provided the protected cysteinyl‐S‐α‐glycosides 6 and 7 in good yields. These S‐α‐glycosylated cysteine derivatives were only available by use of the non‐urethane N‐protected glycosyl acceptors 4 and 5. Palladium‐catalyzed hydrogenolysis and subsequent hydrazinolysis of the benzylated compound 7 afforded L‐cysteinyl‐S‐α‐D‐glucoside 1, a novel S‐glycosyl amino acid.
• Synthesis of <i>S</i>-Linked Glycosyl Amino Acids in Aqueous Solution with Unprotected Carbohydrates
  作者：Scott B. Cohen、Randall L. Halcomb

  DOI：10.1021/ol006908b

  日期：2001.2.1

  [GRAPHICS]The cyclic sulfamidate 5 was synthesized in 60% overall yield from L-serine benzyl ester, Compound 5 reacted cleanly with the sodium thiolate salt of a variety of unprotected 1-thio sugars in aqueous buffer to afford the corresponding S-linked amino acid glycoconjugates in good yields after hydrolysis of the N-sulfates.