D-phenylglycyl-L-phenylalanine | 110267-40-8

• 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-phenylalanine
• 英文别名: R-Phg-S-Phe；(2S)-2-[[(2R)-2-amino-2-phenylacetyl]amino]-3-phenylpropanoic acid
• CAS: 110267-40-8
• 化学式: C₁₇H₁₈N₂O₃
• 分子量: 298.342
• InChiKey: DEFQGBFBFXKLAX-LSDHHAIUSA-N

物化性质

• 熔点：
  238 °C
• 沸点：
  570.2±50.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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-phenylalanine 在 盐酸 、 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 反应 339.0h， 生成 (3R,6S)-3-phenyl-6-(phenylmethyl)piperazine-2,5-dione
  参考文献：
  名称：

  在水介质中青霉素酰基转移酶催化的肽合成：立体异构纯二酮哌嗪的化学酶促途径

  摘要：

  通过在水介质中由青霉素酰基转移酶催化的合成，由d-（-）-制备了一系列通式为d-（-）-苯基甘氨酰-1X的非天然二肽，其中X为天然α-氨基酸。苯甘氨酸酰胺和相应的氨基酸。将二肽转化为相应的二肽酯，然后将其随后自发环化，得到相应的立体异构纯的二酮哌嗪。

  DOI：

  10.1016/j.tetasy.2003.08.011
• 作为产物：
  描述：

  DL-苯丙氨酸 、 左旋苯甘氨酸酰胺 在 bicarbonate buffer 、 E_. coli penicillin amidase (EC 3.5.1.11) 作用下， 生成 D-phenylglycyl-L-phenylalanine
  参考文献：
  名称：

  Determination of the Enantioselectivity for Kinetically Controlled Condensations Catalysed by Amidases and Peptidases

  摘要：

  For kinetically controlled synthetic reactions catalysed by amidases and peptidases, the enantio- or stereoselectivity determined from initial rates with racemic mixtures (E-syn,E-rac) was found to differ from the enantioselectivity determined from measurements with isolated enantiomeric nucleophiles (E-syn). This was observed for kinetically controlled condensation of R-phenyglycineamide with S-, R- and racemic Phe and S-, R- and racemic Leu catalysed by penicillin amidase from E. coli and for kinetically controlled condensation of N-alpha-acetyl-S-tyrosine ethyl ester with S-, R- and racemic AlaNH(2) catalysed by bovine alpha-chymotrypsin. It is shown that only E-syn,E-rac determined with racemic, nucleophiles is an intrinsic enzyme property which should be used to study the influence of the primary structure, physicochemical parameters and immobilisation on biocatalyst enantioselectivity in kinetically controlled synthetic reactions catalysed by these enzymes.

  DOI：

  10.1002/1615-4169(200212)344:10<1115::aid-adsc1115>3.0.co;2-d

文献信息

• Determination of the Enantioselectivity for Kinetically Controlled Condensations Catalysed by Amidases and Peptidases
  作者：Boris Galunsky、Volker Kasche

  DOI：10.1002/1615-4169(200212)344:10<1115::aid-adsc1115>3.0.co;2-d

  日期：2002.12

  For kinetically controlled synthetic reactions catalysed by amidases and peptidases, the enantio- or stereoselectivity determined from initial rates with racemic mixtures (E-syn,E-rac) was found to differ from the enantioselectivity determined from measurements with isolated enantiomeric nucleophiles (E-syn). This was observed for kinetically controlled condensation of R-phenyglycineamide with S-, R- and racemic Phe and S-, R- and racemic Leu catalysed by penicillin amidase from E. coli and for kinetically controlled condensation of N-alpha-acetyl-S-tyrosine ethyl ester with S-, R- and racemic AlaNH(2) catalysed by bovine alpha-chymotrypsin. It is shown that only E-syn,E-rac determined with racemic, nucleophiles is an intrinsic enzyme property which should be used to study the influence of the primary structure, physicochemical parameters and immobilisation on biocatalyst enantioselectivity in kinetically controlled synthetic reactions catalysed by these enzymes.
• Penicillin acylase-catalyzed peptide synthesis in aqueous medium: a chemo-enzymatic route to stereoisomerically pure diketopiperazines
  作者：Andrei Y. Khimiuk、Alexei V. Korennykh、Luuk M. van Langen、Fred van Rantwijk、Roger A. Sheldon、Vytas K. Švedas

  DOI：10.1016/j.tetasy.2003.08.011

  日期：2003.10

  corresponding amino acids. The conversion of the dipeptides to the corresponding dipeptide esters, followed by their subsequent spontaneous cyclization afforded the corresponding stereoisomerically pure diketopiperazines.

  通过在水介质中由青霉素酰基转移酶催化的合成，由d-（-）-制备了一系列通式为d-（-）-苯基甘氨酰-1X的非天然二肽，其中X为天然α-氨基酸。苯甘氨酸酰胺和相应的氨基酸。将二肽转化为相应的二肽酯，然后将其随后自发环化，得到相应的立体异构纯的二酮哌嗪。