N-(4-pentenoyl)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-S-serine | 331754-33-7

• 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: N-(4-pentenoyl)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-S-serine
• CAS: 331754-33-7
• 化学式: C₂₂H₃₁NO₁₃
• 分子量: 517.487
• InChiKey: ICHNDMGFLCHLLN-BIPLRESBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.38
• 重原子数：
  36.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  190.06
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  氯乙腈 、 N-(4-pentenoyl)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-S-serine 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以66%的产率得到N-(4-pentenoyl)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-S-serine cyanomethyl ester
  参考文献：
  名称：

  Studies toward the site specific incorporation of sugars into proteins: Synthesis of glycosylated aminoacyl–tRNAs

  摘要：

  A series of glycosylated serine derivatives was synthesized from peracetylated sugars and Fmoc-protected serine; these were chemically esterified with the tris-(tetrabutylammoniurn) salt of pdCpA. The fully protected and deprotected glycosylated aminoacyl pdCpAs were ligated enzymatically to an abbreviated tRNA (tRNA-C-OH) to provide the title compounds that are key intermediates in the elaboration of glycoproteins using readthrough of a nonsense codon. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00289-5
• 作为产物：
  描述：

  β-D-葡萄糖五乙酸酯 在 哌啶 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 40.58h， 生成 N-(4-pentenoyl)-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-S-serine
  参考文献：
  名称：

  Studies toward the site specific incorporation of sugars into proteins: Synthesis of glycosylated aminoacyl–tRNAs

  摘要：

  A series of glycosylated serine derivatives was synthesized from peracetylated sugars and Fmoc-protected serine; these were chemically esterified with the tris-(tetrabutylammoniurn) salt of pdCpA. The fully protected and deprotected glycosylated aminoacyl pdCpAs were ligated enzymatically to an abbreviated tRNA (tRNA-C-OH) to provide the title compounds that are key intermediates in the elaboration of glycoproteins using readthrough of a nonsense codon. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00289-5