(2S,3S)-2-[2-((2S)-{[(benzyloxy)carbonyl]amino}butanethioamido)-2-methylpropanamido]-3-methylpentanoic acid | 457058-33-2

• 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: (2S,3S)-2-[2-((2S)-{[(benzyloxy)carbonyl]amino}butanethioamido)-2-methylpropanamido]-3-methylpentanoic acid
• 英文别名: Z-Val-Ψ(CS)-Aib-Ile-OH；Cbz-thionoVal-Aib-Ile-OH；(2S,3S)-3-methyl-2-[[2-methyl-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanethioyl]amino]propanoyl]amino]pentanoic acid
• CAS: 457058-33-2
• 化学式: C₂₃H₃₅N₃O₅S
• 分子量: 465.614
• InChiKey: KCSGJLAKHRGGOR-SZMVWBNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  149
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  H-Val-Aib^t-N(Me)Ph 、 (2S,3S)-2-[2-((2S)-{[(benzyloxy)carbonyl]amino}butanethioamido)-2-methylpropanamido]-3-methylpentanoic acid 在 1-羟基苯并三唑 、 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 20.0h， 以45%的产率得到benzyl [1-(2S)-{4,4-dimethyl-5-(2S,3S)-[2-methyl-1-(2-methyl-1-(2S)-{1-methyl-1-[methyl(phenyl)thiocarbamoyl]ethylcarbamoyl}propylcarbamoyl)butylimino]-4,5-dihydro-1,3-thiazol-2-yl}-2-methylpropyl]carbamate
  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-[(1S)-2-methyl-1-(4,5-dihydro-4,4-dimethyl-5-oxo-1,3-thiazol-2-yl)propyl]carbamate 在 lithium hydroxide 、 1-羟基苯并三唑 、 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 172.5h， 生成 (2S,3S)-2-[2-((2S)-{[(benzyloxy)carbonyl]amino}butanethioamido)-2-methylpropanamido]-3-methylpentanoic acid
  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

文献信息

• Formation of 1,3-Thiazol-5(4H)-imines and 1,3-Oxazol-5(4H)-imines in Aib-Containing Thiopeptides
  作者：Roland A. Breitenmoser、Anthony Linden、Heinz Heimgartner

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

  日期：2002.4

  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.