Fmoc-Val-Thr-salicylaldehyde ester | 1220106-65-9

• 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: Fmoc-Val-Thr-salicylaldehyde ester
• 英文别名: Fmoc-Val-Thr-OPh(2-For)；(2-formylphenyl) (2S,3R)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoyl]amino]-3-hydroxybutanoate
• CAS: 1220106-65-9
• 化学式: C₃₁H₃₂N₂O₇
• 分子量: 544.604
• InChiKey: YIGOXJLJZKTPNA-KEFSCGHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Fmoc-Val-Thr-salicylaldehyde ester 、 L-丝氨酸苄酯盐酸盐 在 吡啶 、 溶剂黄146 作用下， 反应 5.0h， 生成 benzyl (4S)-3-((((9H-fluoren-9-yl)methoxy)carbonyl)-L-valyl-L-threonyl)-2-(2-hydroxyphenyl)oxazolidine-4-carboxylate
  参考文献：
  名称：

  Salicylaldehyde Ester-Induced Chemoselective Peptide Ligations: Enabling Generation of Natural Peptidic Linkages at the Serine/Threonine Sites

  摘要：

  A serine/threonine-based chemoselective ligation method is described. It uses an O-salicylaldehyde ester at the C-terminus, reacting with N-terminal serine or threonine to realize peptide ligations. The utility of the O-salicylaldehyde ester enables the rapid coupling reaction and the production of an N,O-benzylidene acetal intermediate, which is readily converted into natural peptidic linkages (Xaa-Ser/Thr) at the ligation site.

  DOI：

  10.1021/ol1003109
• 作为产物：
  描述：

  水杨醛 、 Fmoc-Val-Thr(ox)-OH 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 Fmoc-Val-Thr-salicylaldehyde ester
  参考文献：
  名称：

  Salicylaldehyde Ester-Induced Chemoselective Peptide Ligations: Enabling Generation of Natural Peptidic Linkages at the Serine/Threonine Sites

  摘要：

  A serine/threonine-based chemoselective ligation method is described. It uses an O-salicylaldehyde ester at the C-terminus, reacting with N-terminal serine or threonine to realize peptide ligations. The utility of the O-salicylaldehyde ester enables the rapid coupling reaction and the production of an N,O-benzylidene acetal intermediate, which is readily converted into natural peptidic linkages (Xaa-Ser/Thr) at the ligation site.

  DOI：

  10.1021/ol1003109

文献信息

• Salicylaldehyde Ester-Induced Chemoselective Peptide Ligations: Enabling Generation of Natural Peptidic Linkages at the Serine/Threonine Sites
  作者：Xuechen Li、Hiu Yung Lam、Yinfeng Zhang、Chun Kei Chan

  DOI：10.1021/ol1003109

  日期：2010.4.16

  A serine/threonine-based chemoselective ligation method is described. It uses an O-salicylaldehyde ester at the C-terminus, reacting with N-terminal serine or threonine to realize peptide ligations. The utility of the O-salicylaldehyde ester enables the rapid coupling reaction and the production of an N,O-benzylidene acetal intermediate, which is readily converted into natural peptidic linkages (Xaa-Ser/Thr) at the ligation site.