Z-Aib-Ψ(CS)-Aib-Ile-OMe | 457058-58-1

• 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: Z-Aib-Ψ(CS)-Aib-Ile-OMe
• 英文别名: methyl (2S,3S)-2-[2-({[(benzyloxy)carbonyl]amino}-2-methylpropanethioamido)-2-methylpropanamido]-3-methylpentanoate
• CAS: 457058-58-1
• 化学式: C₂₃H₃₅N₃O₅S
• 分子量: 465.614
• InChiKey: JSSIYIBGFSSDOF-RDJZCZTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  32.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  105.76
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Z-Aib-Ψ(CS)-Aib-Ile-OMe 在 lithium hydroxide 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 34.0h， 生成 methyl (2S)-2-((2S,3S)-2-{2-[(4,4-dimethyl-2-oxo-1,3-oxazolidin-5-yliden)amino]-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-Aib-Ψ(CS)-Aib-N(Me)Ph 在 camphor-10-sulfonic acid 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 240.03h， 生成 Z-Aib-Ψ(CS)-Aib-Ile-OMe
  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