[2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethylamino]-acetic acid benzyl ester | 193156-91-1

• 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-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethylamino]-acetic acid benzyl ester
• CAS: 193156-91-1
• 化学式: C₂₅H₃₃NO₁₁
• 分子量: 523.537
• InChiKey: PGPSQWZDGHAPPU-VPTPGNQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.84
• 重原子数：
  37.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  [2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethylamino]-acetic acid benzyl ester 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Stereoselective synthesis of neo-C-glycopeptide building blocks: Towards a flexible and control-oriented design as probes for carbohydrate-protein interactions

  摘要：

  Neo-C-glycopeptides (1-4) have been synthesized as building blocks to obtain higher neo-C-glycopeptides as probes for studying carbohydrate-protein interactions. A convergent approach for the synthesis of 4 has been developed, in which two galactose units are attached to a glycine derivative in a stepwise procedure (reductive amination followed by amide coupling) and finally coupling to the protected dipeptide having a free amino group on the side chain. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00255-2
• 作为产物：
  描述：

  allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 在 三乙酰氧基硼氢化钠 、 臭氧 、 溶剂黄146 、 N,N-二异丙基乙胺 、 锌 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 [2-((2R,3S,4R,5S,6R)-3,4,5-Triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl)-ethylamino]-acetic acid benzyl ester
  参考文献：
  名称：

  Stereoselective synthesis of neo-C-glycopeptide building blocks: Towards a flexible and control-oriented design as probes for carbohydrate-protein interactions

  摘要：

  Neo-C-glycopeptides (1-4) have been synthesized as building blocks to obtain higher neo-C-glycopeptides as probes for studying carbohydrate-protein interactions. A convergent approach for the synthesis of 4 has been developed, in which two galactose units are attached to a glycine derivative in a stepwise procedure (reductive amination followed by amide coupling) and finally coupling to the protected dipeptide having a free amino group on the side chain. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00255-2

文献信息

• α-Galactose based neoglycopeptides. Inhibition of verotoxin binding to globotriosylceramide
  作者：Prabhat Arya、Kristina M.K. Kutterer、Huiping Qin、Johanne Roby、Michael L. Barnes、Shuqiong Lin、Clifford A. Lingwood、Markus G. Peter

  DOI：10.1016/s0968-0896(99)00226-6

  日期：1999.12

  Solution and solid phase strategies for the synthesis of a-galactose based neoglycopeptide derivatives 2-13 were developed. Neoglycopeptides generated were tested for the inhibition of verotoxin binding to globotriosylceramide (Gb3) using ELISA. Among all of the compounds tested, only the lipid derivatives of neoglycopeptides, 11, 12 and 13 were found to be inhibitors, IC50 = 2.0 mM (11b and 12c) and 0.2 mM (11c and 13c). All of the inhibitors (11b, 11c, 12c and 13c) have a similar branching of the two alpha-galactosyl units at the N-terminal glycine residue of a short peptide and a lipid moiety attached at the C-terminal site. Both of these factors seem to be crucial for the inhibition. It is interesting to note that the inhibitors have only a portion of the natural trisaccharide ligand. The secondary groups either may contribute in sub-site oriented interactions with the protein receptors or may mimic the internal sugar units of the cell-surface ligand, Gb3. (C) 1999 Elsevier Science Ltd. All rights reserved.