HOOC-NH-Aib-Ψ(CS)-Aib-Ile-OH | 457058-59-2

• 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: HOOC-NH-Aib-Ψ(CS)-Aib-Ile-OH
• 英文别名: (2S,3S)-2-[2-(2-carbamido-2-methylpropanethioamido)-2-methylpropanamido]-3-methylpentanoic acid
• CAS: 457058-59-2
• 化学式: C₁₅H₂₇N₃O₅S
• 分子量: 361.462
• InChiKey: WIIBZIKUVNDLHR-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.34
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  127.76
• 氢给体数：
  5.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  L-缬氨酸甲酯盐酸盐 、 HOOC-NH-Aib-Ψ(CS)-Aib-Ile-OH 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以59%的产率得到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：

  benzyl N-<2-<<1,1-dimethyl-2--2-thioxoethyl>amino>-1,1-dimethyl-2-oxoethyl>carbamate 在 lithium hydroxide 、 camphor-10-sulfonic acid 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N-二异丙基乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 258.78h， 生成 HOOC-NH-Aib-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