Z-Gly-Ψ(CS)-Aib-Ile-OH | 457058-53-6

• 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: Z-Gly-Ψ(CS)-Aib-Ile-OH
• 英文别名: (2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}ethanethioamido)-2-methylpropanamido]-3-methylpentanoic acid
• CAS: 457058-53-6
• 化学式: C₂₀H₂₉N₃O₅S
• 分子量: 423.533
• InChiKey: ZRVRWRUPAOBLTJ-BBRMVZONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116.76
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Z-Gly-Ψ(CS)-Aib-Ile-OH 在 硫化氢 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 18.33h， 生成 methyl (2S)-2-{(2S,3S)-2-[2-(2-{[(benzyloxy)carbonyl]amino}methanethioamido)-2-methylpropanethioamido]-3-methylpentanamido}-3-methylbutanoate
  参考文献：
  名称：

  Formation of 1,3-Thiazol-5(4H)-imines and 1,3-Oxazol-5(4H)-imines in Aib-Containing Thiopeptides

  摘要：

  When tripeptides of type Axx'-Aib-Axx-OH were coupled with amino acid methyl esters by means of commonly used coupling reagents, the formation of 1,3-thiazol-5(4H)-imines and 1,3-oxazol-5(411)-imines was observed. With the aim Of understanding which structure elements are required for this reaction, several model peptides have been prepared according to our recently described methodology, a modification of the 'azirine/oxazolone method', followed by selective isomerization of the peptide thioamides. In addition, attempts to prepare peptides that contain more than one C=S group by the same methodology also led to the formation of 1,3-thiazol-5(4H)-imine-containing derivatives. An additional C=S group can be introduced into the peptide, when the 1,3-thiazol-5(4H)-imines were treated with H2S, although mixtures of epimers were obtained. The structures of an endothiohexapeptide, two 1,3-thiazol-5(4H)-imine, and two peptides containing a 1,3-thiazol5(4H)-imine moiety have been established by X-ray crystal-structure analysis.

  DOI：

  10.1002/1522-2675(200204)85:4<990::aid-hlca990>3.0.co;2-6
• 作为产物：
  描述：

  Z-Gly-Ψ(CS)-Aib-Ile-OMe 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 以100%的产率得到Z-Gly-Ψ(CS)-Aib-Ile-OH
  参考文献：
  名称：

  Formation of 1,3-Thiazol-5(4H)-imines and 1,3-Oxazol-5(4H)-imines in Aib-Containing Thiopeptides

  摘要：

  When tripeptides of type Axx'-Aib-Axx-OH were coupled with amino acid methyl esters by means of commonly used coupling reagents, the formation of 1,3-thiazol-5(4H)-imines and 1,3-oxazol-5(411)-imines was observed. With the aim Of understanding which structure elements are required for this reaction, several model peptides have been prepared according to our recently described methodology, a modification of the 'azirine/oxazolone method', followed by selective isomerization of the peptide thioamides. In addition, attempts to prepare peptides that contain more than one C=S group by the same methodology also led to the formation of 1,3-thiazol-5(4H)-imine-containing derivatives. An additional C=S group can be introduced into the peptide, when the 1,3-thiazol-5(4H)-imines were treated with H2S, although mixtures of epimers were obtained. The structures of an endothiohexapeptide, two 1,3-thiazol-5(4H)-imine, and two peptides containing a 1,3-thiazol5(4H)-imine moiety have been established by X-ray crystal-structure analysis.

  DOI：

  10.1002/1522-2675(200204)85:4<990::aid-hlca990>3.0.co;2-6