Fmoc-Phe-Hyp-OH | 1054665-02-9

• 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: Fmoc-Phe-Hyp-OH
• 英文别名: (2S,4R)-1-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]-4-hydroxypyrrolidine-2-carboxylic acid
• CAS: 1054665-02-9
• 化学式: C₂₉H₂₈N₂O₆
• 分子量: 500.551
• InChiKey: MPMGDJONEBDYAB-PBXQCXKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Fmoc-Phe-Hyp-OH 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 二乙胺 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 17.0h， 生成 (2S,4R)-1-((S)-2-Amino-3-phenyl-propionyl)-4-hydroxy-pyrrolidine-2-carboxylic acid methylamide
  参考文献：
  名称：

  The Impact of Pyrrolidine Hydroxylation on the Conformation of Proline-Containing Peptides

  摘要：

  [GRAPHICS]A series of eight dipeptides of the general formula Ac-Phe-Pro*-NHMe was synthesized and the thermodynamics of the cis --> trans isomerization about the central amide bond were studied by NMR. Pro* represents the following prolines: L-proline (Pro), L-trans-4-hydroxyproline (Hyp), L-cis-4-hydroxyproline (hyp), L-cis-4-methoxyproline (hyp[OMe]), L-trans-3-hydroxyproline (3-Hyp), L-cis-3-hydroxyproline (3-hyp), L-2,3-trans-3,4-cis-3,4-dihydroxyproline (DHP), and L-2,3-cis-3,4-trans3,4-dihydroxyproline (dhp). The conformation of the pyrrolidine ring in each case is discussed in light of previous structural studies, analysis of potential stereoelectronic effects, and NMR data. Hydroxy substituents at C-4 have a greater impact on cis --> trans isomerization than analogous substituents at C-3 as a result of the intervening bond distances and bridging groups. The position of the equilibrium and its dependence on temperature are a reflection of both enthalpic and entropic factors, the latter being complicated in this study by an Ar-Pro interaction in the cis conformation. The substituents on the pyrrolidine ring determine the conformation of the five-membered ring, which in turn influences the strength of the Ar-Pro interaction, backbone dihedral angles, and the relative energy of the cis and trans species. The ultimate position of the equilibrium depends on a complex blend of steric, electronic, and conformational factors.

  DOI：

  10.1021/jo0490043
• 作为产物：
  描述：

  Fmoc-L-苯丙氨酸 、 L-羟基脯氨酸 在 N-羟基丁二酰亚胺 、 N,N'-二环己基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 Fmoc-Phe-Hyp-OH
  参考文献：
  名称：

  The Impact of Pyrrolidine Hydroxylation on the Conformation of Proline-Containing Peptides

  摘要：

  [GRAPHICS]A series of eight dipeptides of the general formula Ac-Phe-Pro*-NHMe was synthesized and the thermodynamics of the cis --> trans isomerization about the central amide bond were studied by NMR. Pro* represents the following prolines: L-proline (Pro), L-trans-4-hydroxyproline (Hyp), L-cis-4-hydroxyproline (hyp), L-cis-4-methoxyproline (hyp[OMe]), L-trans-3-hydroxyproline (3-Hyp), L-cis-3-hydroxyproline (3-hyp), L-2,3-trans-3,4-cis-3,4-dihydroxyproline (DHP), and L-2,3-cis-3,4-trans3,4-dihydroxyproline (dhp). The conformation of the pyrrolidine ring in each case is discussed in light of previous structural studies, analysis of potential stereoelectronic effects, and NMR data. Hydroxy substituents at C-4 have a greater impact on cis --> trans isomerization than analogous substituents at C-3 as a result of the intervening bond distances and bridging groups. The position of the equilibrium and its dependence on temperature are a reflection of both enthalpic and entropic factors, the latter being complicated in this study by an Ar-Pro interaction in the cis conformation. The substituents on the pyrrolidine ring determine the conformation of the five-membered ring, which in turn influences the strength of the Ar-Pro interaction, backbone dihedral angles, and the relative energy of the cis and trans species. The ultimate position of the equilibrium depends on a complex blend of steric, electronic, and conformational factors.

  DOI：

  10.1021/jo0490043

文献信息

• The Impact of Pyrrolidine Hydroxylation on the Conformation of Proline-Containing Peptides
  作者：Carol M. Taylor、Renaud Hardré、Patrick J. B. Edwards

  DOI：10.1021/jo0490043

  日期：2005.2.1

  [GRAPHICS]A series of eight dipeptides of the general formula Ac-Phe-Pro*-NHMe was synthesized and the thermodynamics of the cis --> trans isomerization about the central amide bond were studied by NMR. Pro* represents the following prolines: L-proline (Pro), L-trans-4-hydroxyproline (Hyp), L-cis-4-hydroxyproline (hyp), L-cis-4-methoxyproline (hyp[OMe]), L-trans-3-hydroxyproline (3-Hyp), L-cis-3-hydroxyproline (3-hyp), L-2,3-trans-3,4-cis-3,4-dihydroxyproline (DHP), and L-2,3-cis-3,4-trans3,4-dihydroxyproline (dhp). The conformation of the pyrrolidine ring in each case is discussed in light of previous structural studies, analysis of potential stereoelectronic effects, and NMR data. Hydroxy substituents at C-4 have a greater impact on cis --> trans isomerization than analogous substituents at C-3 as a result of the intervening bond distances and bridging groups. The position of the equilibrium and its dependence on temperature are a reflection of both enthalpic and entropic factors, the latter being complicated in this study by an Ar-Pro interaction in the cis conformation. The substituents on the pyrrolidine ring determine the conformation of the five-membered ring, which in turn influences the strength of the Ar-Pro interaction, backbone dihedral angles, and the relative energy of the cis and trans species. The ultimate position of the equilibrium depends on a complex blend of steric, electronic, and conformational factors.