(2S)-N-[(2S)-6-amino-1-[(2S)-5-carbamimidamido-1-hydroxy-1-[(2S)-1-hydroxy-1-[(2S)-1-hydroxy-1-[2-hydroxy-2-[(2S)-1-oxo-1-phenylsulfanylpropan-2-yl]iminoethyl]imino-3-phenylpropan-2-yl]imino-3-(1H-imidazol-5-yl)propan-2-yl]iminopentan-2-yl]imino-1-hydroxyhexan-2-yl]-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[9H-fluoren-9-ylmethoxy(hydroxy)methylidene]amino]-1-hydroxy-3-methylbutylidene]amino]-1,3-dihydroxybutylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxypropylidene]amino]pentanediimidic acid | 1220106-94-4

• 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: (2S)-N-[(2S)-6-amino-1-[(2S)-5-carbamimidamido-1-hydroxy-1-[(2S)-1-hydroxy-1-[(2S)-1-hydroxy-1-[2-hydroxy-2-[(2S)-1-oxo-1-phenylsulfanylpropan-2-yl]iminoethyl]imino-3-phenylpropan-2-yl]imino-3-(1H-imidazol-5-yl)propan-2-yl]iminopentan-2-yl]imino-1-hydroxyhexan-2-yl]-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[9H-fluoren-9-ylmethoxy(hydroxy)methylidene]amino]-1-hydroxy-3-methylbutylidene]amino]-1,3-dihydroxybutylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxypropylidene]amino]pentanediimidic acid
• CAS: 1220106-94-4
• 化学式: C₇₃H₉₈N₁₈O₁₆S
• 分子量: 1515.76
• InChiKey: FXGFUNDIYPBXLH-FJOXVHQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  108
• 可旋转键数：
  46
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  611
• 氢给体数：
  20
• 氢受体数：
  32

反应信息

• 作为产物：
  描述：

  Fmoc-Val-Thr-salicylaldehyde ester 、 H-Ser-Ala-Gln-Lys-Arg-His-Phe-Gly-Ala-SPh 在 吡啶 、 溶剂黄146 、 三异丙基硅烷 、 水 、 三氟乙酸 作用下， 反应 6.08h， 以72%的产率得到(2S)-N-[(2S)-6-amino-1-[(2S)-5-carbamimidamido-1-hydroxy-1-[(2S)-1-hydroxy-1-[(2S)-1-hydroxy-1-[2-hydroxy-2-[(2S)-1-oxo-1-phenylsulfanylpropan-2-yl]iminoethyl]imino-3-phenylpropan-2-yl]imino-3-(1H-imidazol-5-yl)propan-2-yl]iminopentan-2-yl]imino-1-hydroxyhexan-2-yl]-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[9H-fluoren-9-ylmethoxy(hydroxy)methylidene]amino]-1-hydroxy-3-methylbutylidene]amino]-1,3-dihydroxybutylidene]amino]-1,3-dihydroxypropylidene]amino]-1-hydroxypropylidene]amino]pentanediimidic acid
  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.