N-<3-(Pyrrol-1-yl)propanoyl>-L-cysteine methyl ester | 142056-26-6

• 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: N-<3-(Pyrrol-1-yl)propanoyl>-L-cysteine methyl ester
• 英文别名: N-(3-pyrrole-1-yl)propanoyl-L-cysteine methylester；methyl (2R)-2-(3-pyrrol-1-ylpropanoylamino)-3-sulfanylpropanoate
• CAS: 142056-26-6
• 化学式: C₁₁H₁₆N₂O₃S
• 分子量: 256.326
• InChiKey: JWTGXABQRYEUPG-VIFPVBQESA-N

物化性质

• 沸点：
  447.6±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  61.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二氯二茂钼 、 N-<3-(Pyrrol-1-yl)propanoyl>-L-cysteine methyl ester 在 三乙胺 作用下， 以 乙醇 为溶剂， 以75%的产率得到
  参考文献：
  名称：

  Ligand rotamers and redox isomerism: metallo-pseudo-prolines

  摘要：

  配体旋转可使酰胺基团的氧原子朝向或远离邻近的金属中心，从而使旋转体 A 和 B 的 E°电位相差 150 mV；B 的金属中心氧化可使系统从旋转体相对数量差异很小的状态转变为顺式酰胺构象占主导地位的状态；这种新的金属环系统可被视为具有氧化还原敏感旋转体特性的伪脯氨酸。

  DOI：

  10.1039/a706634a
• 作为产物：
  描述：

  吡咯-1-丙酸 在 N,N'-二环己基碳二亚胺 、 1,4-二巯基-2,3-丁二醇 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 N-<3-(Pyrrol-1-yl)propanoyl>-L-cysteine methyl ester
  参考文献：
  名称：

  Synthesis and anodic polymerisation of an L-cystine derivatised pyrrole; copolymerisation with a tetraalkylammonium pyrrole allows reduction of the cystinyl film to a cysteinyl state that binds electroactive {Fe4S4}2+ centres

  摘要：

  合成胱氨酸衍生吡咯 I，并在铂和玻璃碳电极上通过阳极氧化作用生成稳定的中性聚合物或阳离子共聚物；对胱氨酸-四烷基铵共官能化薄膜进行化学还原，可得到带有胱氨酰基团的离子交换聚合物。

  DOI：

  10.1039/c39920000694

文献信息

• Synthesis and anodic polymerisation of an L-cystine derivatised pyrrole; copolymerisation with a tetraalkylammonium pyrrole allows reduction of the cystinyl film to a cysteinyl state that binds electroactive {Fe4S4}2+ centres
  作者：Christopher J. Pickett、Karl S. Ryder、Jean-Claude Moutet

  DOI：10.1039/c39920000694

  日期：——

  The cystine derivatised pyrrole I is synthesised and stable neutral polymers or cationic copolymers are produced by anodic oxidation at Pt and glassy carbon electrodes; chemical reduction of cystine–tetraalkylammonium co-functionalised films gives ion-exchange polymers with pendant cysteinyl groups and these thiolate films tightly bind Fe4S4}2+ centres giving an electrode–polymer assembly with electroactive, cysteinyl ligated, ferredoxin-like units.

  合成胱氨酸衍生吡咯 I，并在铂和玻璃碳电极上通过阳极氧化作用生成稳定的中性聚合物或阳离子共聚物；对胱氨酸-四烷基铵共官能化薄膜进行化学还原，可得到带有胱氨酰基团的离子交换聚合物。
• Bioinorganic reaction centres on electrodes. Modified electrodes possessing amino acid, peptide and ferredoxin-type groups on a poly(pyrrole) backbone
  作者：Christopher J. Pickett、Karl S. Ryder

  DOI：10.1039/dt9940002181

  日期：——

  Some amino-acid and peptide derivatives of pyrrole such as the N,N'-bisN-[3-pyrrol-1-yl)propanoyl]-glycyl}-L-cystine methyl ester have been synthesised and characterised. The functionalised pyrroles undergo facile electropolymerisation to give electrode-bound films which are conducting in the oxidised state. Cystine-derivatised co-polymers can be converted to a cysteinyl state which allows the binding of ferredoxin centres. Activated pentafluorophenyl esters provide a convenient route to the amino-acid and peptide derivatised monomers. Importantly, electropolymerisation of an active ester allows covalent modification of electrode-bound films after polymerisation with, for example, redox-active ferrocenemethanol.
• Ligand rotamers and redox isomerism: metallo-pseudo-prolines
  作者：Marcus C. Durrant、Shirley A. Fairhurst、David L. Hughes、Saad K. Ibrahim、Mario Passos、Christopher J. Pickett、Mario Passos、Arlete Queiros

  DOI：10.1039/a706634a

  日期：——

  A ligand rotation which orientates the oxygen atom of an amide group towards or away from a neighbouring metal centre provides rotamers A and B with E° potentials which differ by 150 mV; oxidation of the metal centre of B switches the system from a state in which there is a small difference in the relative populations of the rotamers to one in which the cis-amide conformation greatly predominates; this new metallocycle system can be viewed as a pseudo-proline with redox sensitive rotameric properties.

  配体旋转可使酰胺基团的氧原子朝向或远离邻近的金属中心，从而使旋转体 A 和 B 的 E°电位相差 150 mV；B 的金属中心氧化可使系统从旋转体相对数量差异很小的状态转变为顺式酰胺构象占主导地位的状态；这种新的金属环系统可被视为具有氧化还原敏感旋转体特性的伪脯氨酸。