S-α-D-ribosyl-L-homocysteine trifluoroacetic acid | 1618645-74-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-α-D-ribosyl-L-homocysteine trifluoroacetic acid
• CAS: 1618645-74-1
• 化学式: C₂HF₃O₂*C₉H₁₇NO₆S
• 分子量: 381.327
• InChiKey: OEWKMNSCHBQNAO-XFWLUUOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.41
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  170.54
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  卡培他滨杂质25 在 盐酸 、 双(三甲基硅烷基)氨基钾 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 14.17h， 生成 S-α-D-ribosyl-L-homocysteine trifluoroacetic acid 、 S-β-D-ribosyl-L-homocysteine trifluoroacetic acid
  参考文献：
  名称：

  Revisiting synthetic preparation of the quorum sensing substrate S-d-ribosyl-l-homocysteine (SRH)

  摘要：

  Cleavage of the thioether bond of S-D-ribosyl-L-homocysteine (SRH) by the enzyme S-ribosylhomocysteinase (LuxS) serves as the final biosynthetic step in the generation of the quorum sensing autoinducer AI-2 by bacteria. Herein, a revised chemical synthesis of SRH is presented at convenient scale and purity for in vitro studies of LuxS. Potassium bis(trimethylsilyl) amide (KHMDS) is identified as a judicious base for the formation of the thioether of the target compound from readily-accessible precursors: a thiol nucleophile derived from L-homocystine and a sulfonate-activated D-ribosyl electrophile. The exclusive use of acid-labile protecting groups allows for facile deprotection to the final product, producing the TFA salt of SRH in five synthetic steps and 26% overall yield. The chemically-synthesized material is isolated at high purity and demonstrated to serve as the LuxS substrate by an in vitro assay. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.009