Asparagine, N-carbobenzyloxy- | 4668-37-5

• 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: Asparagine, N-carbobenzyloxy-
• 英文别名: methyl 4-amino-4-oxo-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 4668-37-5
• 化学式: C₁₃H₁₆N₂O₅
• mdl: MFCD00743485
• 分子量: 280.28
• InChiKey: CQIPRSHYISKHFR-UHFFFAOYSA-N

物化性质

• 熔点：
  150 °C
• 沸点：
  537.3±50.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Asparagine, N-carbobenzyloxy- 在 sodium hydroxide 、 Alcalase 2.4L from Bacillus sp 、 sodium hydride 、 sodium chloride 作用下， 以 四氢呋喃 、 phosphate buffer 为溶剂， 反应 5.43h， 生成 (R)-(1-benzyl-2,5-dioxo-pyrrolidin-3-yl)carbamic acid benzyl ester
  参考文献：
  名称：

  Chemo-enzymatic preparation of chiral 3-aminopyrrolidine derivatives

  摘要：

  A new simple method for the enantioselective enzymatic hydrolysis of N-protected D-asparagine esters suitable for the use on the preparative scale is presented. Due to major obstacles observed under conventional reaction conditions-racemization of the retained ester and a strong enzyme inactivation-a comparatively low pH together with an organic co-solvent had to be employed. Under these conditions, nearly all tested proteases demonstrated good activity and excellent enantioselectivity giving access to the corresponding D-esters and L-asparagines in high optical purities (>95% ee) and good chemical yields (>40%). From the unnatural D-asparagine derivative, sequential cyclization, selective deprotection and reduction yielded efficiently benzyl protected (R)-3-aminopyrrolidine, a homo-chiral building block utilized in numerous drug candidates. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.118
• 作为产物：
  描述：

  甲醇 、 Z-DL-天冬酰胺酸 在 氯化亚砜 作用下， 反应 0.25h， 以91%的产率得到Asparagine, N-carbobenzyloxy-
  参考文献：
  名称：

  Chemo-enzymatic preparation of chiral 3-aminopyrrolidine derivatives

  摘要：

  A new simple method for the enantioselective enzymatic hydrolysis of N-protected D-asparagine esters suitable for the use on the preparative scale is presented. Due to major obstacles observed under conventional reaction conditions-racemization of the retained ester and a strong enzyme inactivation-a comparatively low pH together with an organic co-solvent had to be employed. Under these conditions, nearly all tested proteases demonstrated good activity and excellent enantioselectivity giving access to the corresponding D-esters and L-asparagines in high optical purities (>95% ee) and good chemical yields (>40%). From the unnatural D-asparagine derivative, sequential cyclization, selective deprotection and reduction yielded efficiently benzyl protected (R)-3-aminopyrrolidine, a homo-chiral building block utilized in numerous drug candidates. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.10.118

文献信息

• Spontaneous cyclization of a chain shortened lysine analog
  作者：S Ranganathan、D Ranganathan、W.P Singh

  DOI：10.1016/0040-4039(88)85099-8

  日期：1988.1

  The chain shortened analog of lysine, H2NCH2CH2CH(NHZ)COOR, generated from N-protected glutamine esters, undergoes spontaneous cyclization. The results show that amino acids having H2NCH2CH2 - side chains cannot be supported on tRNA and provides a rationale for keeping the amino group of lysine by as many as four méthylènes away from the peptide backbone.

  由N保护的谷氨酰胺酯生成的赖氨酸链缩短的类似物H 2 NCH 2 CH 2 CH（NHZ）COOR进行自发环化。结果表明，具有H 2 NCH 2 CH 2-侧链的氨基酸不能在tRNA上得到支持，并且为将赖氨酸的氨基与肽主链保持多达四个甲硫基的氨基酸提供了原理。
• IVANYI, GEZA;SCHON, ISTVAN;SZIRTES, TAMAS;UBERHARDT, TAMAS;KOVACS, LAJOS
  作者：IVANYI, GEZA、SCHON, ISTVAN、SZIRTES, TAMAS、UBERHARDT, TAMAS、KOVACS, LAJOS

  DOI：——

  日期：——
• Chemo-enzymatic preparation of chiral 3-aminopyrrolidine derivatives
  作者：Hans Iding、Beat Wirz、Mark Rogers-Evans

  DOI：10.1016/j.tet.2003.10.118

  日期：2004.1

  A new simple method for the enantioselective enzymatic hydrolysis of N-protected D-asparagine esters suitable for the use on the preparative scale is presented. Due to major obstacles observed under conventional reaction conditions-racemization of the retained ester and a strong enzyme inactivation-a comparatively low pH together with an organic co-solvent had to be employed. Under these conditions, nearly all tested proteases demonstrated good activity and excellent enantioselectivity giving access to the corresponding D-esters and L-asparagines in high optical purities (>95% ee) and good chemical yields (>40%). From the unnatural D-asparagine derivative, sequential cyclization, selective deprotection and reduction yielded efficiently benzyl protected (R)-3-aminopyrrolidine, a homo-chiral building block utilized in numerous drug candidates. (C) 2003 Elsevier Ltd. All rights reserved.