D-phenylglycyl-L-phenylglycine | 737745-61-8

• 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: D-phenylglycyl-L-phenylglycine
• 英文别名: Glycine, (2R)-2-phenylglycyl-2-phenyl-, (2S)-；(2S)-2-[[(2R)-2-amino-2-phenylacetyl]amino]-2-phenylacetic acid
• CAS: 737745-61-8
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: UYKXJEVQVZFVPB-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  D-phenylglycyl-L-phenylglycine 在 盐酸 、 氢氧化钾 作用下， 反应 7.0h， 生成 D,L-3,6-diphenylpiperazine-2,5-diphenylpiperazine-2,5-dione
  参考文献：
  名称：

  Penicillin acylase-catalyzed peptide synthesis: a chemo-enzymatic route to stereoisomers of 3,6-diphenylpiperazine-2,5-dione

  摘要：

  Chiral dipeptides of phenylglycine were synthesized using immobilized Escherichia coli penicillin acylase. The high selectivity of penicillin acylase for L-amino acids as the nucleophile resulted in the efficient acylation of L-phenylglycine by D-phenylglycine amide at pH 9.7 to give D-phenylglycyl-L-phenylglycine in 69% yield. No isomers or tripeptides were formed. The low enantiospecificity of the enzyme for the acyl donor provided the possibility of preparing the corresponding L,L-dipeptides, starting from L-phenylglycine methyl ester as both donor and acceptor at pH 7.5, resulting in a 63% yield of L-phenylglycyl-Lphenylglycine methyl ester. The product precipitated under the reaction conditions; this effectively prevented the formation of oligomers as well as chemical transformation of the product.The dipeptide esters of phenylglycine easily cyclized to diketopiperazines in aqueous methanol. L-Pheny-glycyl-L-phenylglycine methyl ester formed L,L-3,6-diphenylpiperazine-2,5-dione (cis); the achiral trans isomer was obtained from D-phenylglycyl-L-phenylglycine methyl ester. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00027-6
• 作为产物：
  描述：

  左旋苯甘氨酸酰胺 、 L-苯甘氨酸 在 immobilized Escherichia coli penicillin acylase 作用下， 以 ammonium hydroxide 为溶剂， 以69%的产率得到D-phenylglycyl-L-phenylglycine
  参考文献：
  名称：

  Penicillin acylase-catalyzed peptide synthesis: a chemo-enzymatic route to stereoisomers of 3,6-diphenylpiperazine-2,5-dione

  摘要：

  Chiral dipeptides of phenylglycine were synthesized using immobilized Escherichia coli penicillin acylase. The high selectivity of penicillin acylase for L-amino acids as the nucleophile resulted in the efficient acylation of L-phenylglycine by D-phenylglycine amide at pH 9.7 to give D-phenylglycyl-L-phenylglycine in 69% yield. No isomers or tripeptides were formed. The low enantiospecificity of the enzyme for the acyl donor provided the possibility of preparing the corresponding L,L-dipeptides, starting from L-phenylglycine methyl ester as both donor and acceptor at pH 7.5, resulting in a 63% yield of L-phenylglycyl-Lphenylglycine methyl ester. The product precipitated under the reaction conditions; this effectively prevented the formation of oligomers as well as chemical transformation of the product.The dipeptide esters of phenylglycine easily cyclized to diketopiperazines in aqueous methanol. L-Pheny-glycyl-L-phenylglycine methyl ester formed L,L-3,6-diphenylpiperazine-2,5-dione (cis); the achiral trans isomer was obtained from D-phenylglycyl-L-phenylglycine methyl ester. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00027-6

文献信息

• Penicillin acylase-catalyzed peptide synthesis: a chemo-enzymatic route to stereoisomers of 3,6-diphenylpiperazine-2,5-dione
  作者：Luuk M van Langen、Fred van Rantwijk、Vytas K Švedas、Roger A Sheldon

  DOI：10.1016/s0957-4166(00)00027-6

  日期：2000.3

  Chiral dipeptides of phenylglycine were synthesized using immobilized Escherichia coli penicillin acylase. The high selectivity of penicillin acylase for L-amino acids as the nucleophile resulted in the efficient acylation of L-phenylglycine by D-phenylglycine amide at pH 9.7 to give D-phenylglycyl-L-phenylglycine in 69% yield. No isomers or tripeptides were formed. The low enantiospecificity of the enzyme for the acyl donor provided the possibility of preparing the corresponding L,L-dipeptides, starting from L-phenylglycine methyl ester as both donor and acceptor at pH 7.5, resulting in a 63% yield of L-phenylglycyl-Lphenylglycine methyl ester. The product precipitated under the reaction conditions; this effectively prevented the formation of oligomers as well as chemical transformation of the product.The dipeptide esters of phenylglycine easily cyclized to diketopiperazines in aqueous methanol. L-Pheny-glycyl-L-phenylglycine methyl ester formed L,L-3,6-diphenylpiperazine-2,5-dione (cis); the achiral trans isomer was obtained from D-phenylglycyl-L-phenylglycine methyl ester. (C) 2000 Elsevier Science Ltd. All rights reserved.