H2N-L-Ala-L-Pyr-OBn | 363139-42-8

• 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: H2N-L-Ala-L-Pyr-OBn
• 英文别名: benzyl (2S)-1-[(2S)-2-aminopropanoyl]-5-oxopyrrolidine-2-carboxylate
• CAS: 363139-42-8
• 化学式: C₁₅H₁₈N₂O₄
• 分子量: 290.319
• InChiKey: GYJICEBWXJJZMZ-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  89.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  叔丁氧羰基丙氨酸五氟苯基酯 、 H2N-L-Ala-L-Pyr-OBn 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到Boc-L-Ala-L-ALa-L-Pyr-OBn
  参考文献：
  名称：

  Pyroglutamic acid as a pseudoproline moiety: a facile method for its introduction into polypeptide chains

  摘要：

  The acylation of benzyl (S)-pyroglutamate is reported by reaction with the pentafluorophenyl ester of protected alanine and threonine. The H-1 NMR analysis of the acylated products shows that the alpha hydrogens of the protected amino acids are very deshielded. This effect is due to the presence of the carbonyl of the lactam ring and shows that the peptide bond is in the trans conformation. The deprotection of the amino acids is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00981-9
• 作为产物：
  描述：

  (2S)-5-氧代脯氨酸苄酯 在 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 H2N-L-Ala-L-Pyr-OBn
  参考文献：
  名称：

  Pyroglutamic acid as a pseudoproline moiety: a facile method for its introduction into polypeptide chains

  摘要：

  The acylation of benzyl (S)-pyroglutamate is reported by reaction with the pentafluorophenyl ester of protected alanine and threonine. The H-1 NMR analysis of the acylated products shows that the alpha hydrogens of the protected amino acids are very deshielded. This effect is due to the presence of the carbonyl of the lactam ring and shows that the peptide bond is in the trans conformation. The deprotection of the amino acids is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00981-9

文献信息

• Pyroglutamic acid as a pseudoproline moiety: a facile method for its introduction into polypeptide chains
  作者：Claudia Tomasini、Marzia Villa

  DOI：10.1016/s0040-4039(01)00981-9

  日期：2001.7

  The acylation of benzyl (S)-pyroglutamate is reported by reaction with the pentafluorophenyl ester of protected alanine and threonine. The H-1 NMR analysis of the acylated products shows that the alpha hydrogens of the protected amino acids are very deshielded. This effect is due to the presence of the carbonyl of the lactam ring and shows that the peptide bond is in the trans conformation. The deprotection of the amino acids is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.