Ac-Cys(1)-Pro-D-Val-Cys(1)-NH2 | 125768-50-5

• 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: Ac-Cys(1)-Pro-D-Val-Cys(1)-NH2
• 英文别名: (3R,8R,11R,14S)-3-acetamido-2,10,13-trioxo-11-propan-2-yl-5,6-dithia-1,9,12-triazabicyclo[12.3.0]heptadecane-8-carboxamide
• CAS: 125768-50-5
• 化学式: C₁₈H₂₉N₅O₅S₂
• 分子量: 459.591
• InChiKey: OPNDLSUTIKYNIH-XDQVBPFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  201
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  Ac-Cys(Phacm)-Pro-D-Val-Cys(Phacm)-NH2 在 penicillin amidohydrolase 作用下， 生成 Ac-Cys(1)-Pro-D-Val-Cys(1)-NH2
  参考文献：
  名称：

  S-Phenylacetamidomethyl (Phacm): an orthogonal cysteine protecting group for Boc and Fmoc solid-phase peptide synthesis strategies

  摘要：

  The reliability of the S-phenylacetamidomethyl-L-cysteine Cys(Phacm), a versatile derivative compatible with both Boc and Fmoc protection schemes, has been examined for solid-phase peptide synthesis. The Phacm group has the same properties as acetamidomethyl (Acm) and in addition is cleaved by the action of the enzyme penicillin amidohydrolase. Thus, Phacm is orthogonal with the common cysteine-protecting groups, such as 4-methylbenzyl (p-MeBzl), trityl (Trt) and fluorenylmethyl (Fm).

  DOI：

  10.1039/p19950001095

文献信息

• Convenient synthesis of a cyclic peptide disulfide: A type II β-turn structural model
  作者：Carlos García-Echeverría、Fernando Albericio、Miquel Pons、George Barany、Ernest Giralt

  DOI：10.1016/s0040-4039(01)80422-6

  日期：——
• S-Phenylacetamidomethyl (Phacm): an orthogonal cysteine protecting group for Boc and Fmoc solid-phase peptide synthesis strategies
  作者：Miriam Royo、Jordi Alsina、Ernest Giralt、Urszula Slomcyznska、Fernando Albericio

  DOI：10.1039/p19950001095

  日期：——

  The reliability of the S-phenylacetamidomethyl-L-cysteine Cys(Phacm), a versatile derivative compatible with both Boc and Fmoc protection schemes, has been examined for solid-phase peptide synthesis. The Phacm group has the same properties as acetamidomethyl (Acm) and in addition is cleaved by the action of the enzyme penicillin amidohydrolase. Thus, Phacm is orthogonal with the common cysteine-protecting groups, such as 4-methylbenzyl (p-MeBzl), trityl (Trt) and fluorenylmethyl (Fm).