(2S,3S)-2-(2-{2-[(2S,3S)-2-((2S)-{[(tert-butoxy)carbonyl]amino}-3-(indol-3-yl)propanamido)-3-methylpentanamido]ethanethioamido}-2-methylpropanamido)-3-methylpentanoic acid | 259217-30-6

• 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: (2S,3S)-2-(2-{2-[(2S,3S)-2-((2S)-{[(tert-butoxy)carbonyl]amino}-3-(indol-3-yl)propanamido)-3-methylpentanamido]ethanethioamido}-2-methylpropanamido)-3-methylpentanoic acid
• 英文别名: Boc-Trp-Ile-Ala-Ψ(CS)-Aib-Ile-OH；Boc-Trp-Ile-thionoAla-Aib-Ile-OH；(2S,3S)-2-[[2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-3-methylpentanoyl]amino]propanethioyl]amino]-2-methylpropanoyl]amino]-3-methylpentanoic acid
• CAS: 259217-30-6
• 化学式: C₃₅H₅₄N₆O₇S
• 分子量: 702.916
• InChiKey: HMPLYMOLDRIPRU-LHYRVYERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  49
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  223
• 氢给体数：
  7
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2-(2-{2-[(2S,3S)-2-((2S)-{[(tert-butoxy)carbonyl]amino}-3-(indol-3-yl)propanamido)-3-methylpentanamido]ethanethioamido}-2-methylpropanamido)-3-methylpentanoic acid 在 水 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 正己烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 17.0h， 生成 methyl (2S)-2-[(2S,3S)-2-(2-{(2S)-2-[(2S,3S)-2-((2S)-{[(tert-butoxy)carbonyl]amino}-3-(indol-3-yl)propanamido)-3-methylpentanamido]propanamido}-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：

  L-异亮氨酸甲酯盐酸盐 在 lithium hydroxide 、 水 、 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 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 23.0h， 生成 (2S,3S)-2-(2-{2-[(2S,3S)-2-((2S)-{[(tert-butoxy)carbonyl]amino}-3-(indol-3-yl)propanamido)-3-methylpentanamido]ethanethioamido}-2-methylpropanamido)-3-methylpentanoic acid
  参考文献：
  名称：

  Synthesis of Endothiopeptides and Their Cyclization to 1,3-Thiazol-5(4H)-imines

  摘要：

  Further investigations of the synthesis of endothio analogues of the segment 1-10 (8) of an apolar analogon of zervamicin IIA are described. The endothiodecapeptide Boc-Trp-Ile-Ala-Aib-Ile-Val-Aib-Leu-Aib-Psi(CS)-Pro-OMe (10) has been prepared in good yield by our novel methodology. On the other hand, all attempts to prepare endothio analogues of 8 with the thioamide group at position 3 (Ala') gave not the expected linear endothiopeptides but led to epimerized 1,3-thiazol-5(4H)-imine derivatives as the main products. The mixture of epimers of the thiazolimines 27, 30, and 31 have been separated by means of preparative HPLC, and their structures have been established by 2D-NMR experiments.

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<1899::aid-hlca1899>3.0.co;2-m