Boc-Leu-Ile-Val-OH | 591733-86-7

• 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: Boc-Leu-Ile-Val-OH
• 英文别名: N-(tert-Butoxycarbonyl)-L-leucyl-L-isoleucyl-L-valine；(2S)-3-methyl-2-[[(2S,3S)-3-methyl-2-[[(2S)-4-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]pentanoyl]amino]butanoic acid
• CAS: 591733-86-7
• 化学式: C₂₂H₄₁N₃O₆
• 分子量: 443.584
• InChiKey: UIOIKIGWDSZGNB-QAETUUGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-Methyl-2-[2-((E)-3-(S)-pyrrolidin-2-yl-acryloylamino)-acetylamino]-pentanoic acid methyl ester 、 Boc-Leu-Ile-Val-OH 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 (S)-2-{2-[(E)-3-((S)-1-{(S)-2-[(2S,3S)-2-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-3-methyl-pentanoylamino]-3-methyl-butyryl}-pyrrolidin-2-yl)-acryloylamino]-acetylamino}-4-methyl-pentanoic acid methyl ester
  参考文献：
  名称：

  Nucleation of β-Hairpin Structures with Cis Amide Bonds in E-Vinylogous Proline-Containing Peptides

  摘要：

  Synthesis and conformational studies of peptides containing the E-vinylogous prolines 1 (VPro1) and 2 (VPro2), Boc-Ala-Val-VPro1-Xaa-Leu-OMe (3, Xaa = Gly; 4, Xaa = Phe), Boc-Ala-Val-VPro2-Xaa-Leu-OMe (5, Xaa = Gly; 6, Xaa = Phe), Boc-Leu-Ile-Val-VPro1-Xaa-Leu-OMe (7, Xaa = Gly; 8, Xaa = Phe), and Boc-Leu-Ile-Val-VPro2-Xaa-Leu-OMe (9, Xaa = Gly; 10, Xaa = Phe), were carried out. It has been shown that both VPro1 and VPro2 lead to the formation of 12-membered intramolecularly hydrogen bonded structures very similar to type VI beta-turns with a cis Xaa-VPro amide bond in the major conformers in all the peptides 3-10, resulting in the nucleation of beta-hairpin type structures in these molecules in CDCl3.

  DOI：

  10.1021/jo034361j

文献信息

• Nucleation of <i>β</i>-Hairpin Structures with Cis Amide Bonds in <i>E</i>-Vinylogous Proline-Containing Peptides
  作者：Tushar K. Chakraborty、Animesh Ghosh、S. Kiran Kumar、Ajit C. Kunwar

  DOI：10.1021/jo034361j

  日期：2003.8.1

  Synthesis and conformational studies of peptides containing the E-vinylogous prolines 1 (VPro1) and 2 (VPro2), Boc-Ala-Val-VPro1-Xaa-Leu-OMe (3, Xaa = Gly; 4, Xaa = Phe), Boc-Ala-Val-VPro2-Xaa-Leu-OMe (5, Xaa = Gly; 6, Xaa = Phe), Boc-Leu-Ile-Val-VPro1-Xaa-Leu-OMe (7, Xaa = Gly; 8, Xaa = Phe), and Boc-Leu-Ile-Val-VPro2-Xaa-Leu-OMe (9, Xaa = Gly; 10, Xaa = Phe), were carried out. It has been shown that both VPro1 and VPro2 lead to the formation of 12-membered intramolecularly hydrogen bonded structures very similar to type VI beta-turns with a cis Xaa-VPro amide bond in the major conformers in all the peptides 3-10, resulting in the nucleation of beta-hairpin type structures in these molecules in CDCl3.