(2R,3S)-<3-2H1>-phenylalanine | 39236-18-5

• 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: (2R,3S)-<3-2H1>-phenylalanine
• 英文别名: (2R,3S)-2-amino-3-deuterio-3-phenylpropanoic acid
• CAS: 39236-18-5
• 化学式: C₉H₁₁NO₂
• 分子量: 166.184
• InChiKey: COLNVLDHVKWLRT-WVCCJZRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-<3-2H1>-phenylalanine 反应 192.0h， 以70%的产率得到1,3-二氯-1,1,2,2,3-五氟丙烷
  参考文献：
  名称：

  Synthesis of each stereoisomer of [3-2H1]phenylalanine and evaluation of the stereochemical course of the reaction of (R)-phenylalanine with (S)-phenylalanine ammonia-lyase

  摘要：

  The four stereoisomers of [3-H-2(1)] phenylalanine have been prepared. each as a single enantiomer in ca. 98% diastereoisomeric excess and with ca. 99% deuterium incorporation, by Side-chain bromination of phenylalanine derivatives, followed by deuteriolysis of each of the diastereoisomeric product bromides with deuterium over 5% palladium-on-carbon. The latter reactions, proceeded with retention of : configuration. (2R,3S)-[3-H-2(1)] Phenylalanine reacted with (S)-phenylalanine ammonia-lyase to give [3-H-2(1)] -trans-cinnamic acid, with 92% deuterium incorporation; while the (2R,3R) -stereoisomer of the deuteriated phenylalanine gave [3-H-2(1)] -trans-cinnamic acid with 27% deuterium incorporation. These results indicate that reaction of (R)-phenylalanine with the enzyme involves mainly loss of the 3-pro-R hydrogen and ammonia, in an antiperiplanar elimination process analogous to that previously reported for (S)-phenylalanine,while a minor pathway for reaction of :(R)-phenylalanine is either isomerization to (S)-phenylalanine; before elimination, or synperiplanar elimination.

  DOI：

  10.1039/p19940003545
• 作为产物：
  描述：

  (2R,3S)-<3-2H1>-N-phthaloylphenylalanine methyl ester 在 盐酸 、 溶剂黄146 作用下， 反应 6.0h， 生成 (2R,3S)-<3-2H1>-phenylalanine
  参考文献：
  名称：

  Synthesis of each stereoisomer of [3-2H1]phenylalanine and evaluation of the stereochemical course of the reaction of (R)-phenylalanine with (S)-phenylalanine ammonia-lyase

  摘要：

  The four stereoisomers of [3-H-2(1)] phenylalanine have been prepared. each as a single enantiomer in ca. 98% diastereoisomeric excess and with ca. 99% deuterium incorporation, by Side-chain bromination of phenylalanine derivatives, followed by deuteriolysis of each of the diastereoisomeric product bromides with deuterium over 5% palladium-on-carbon. The latter reactions, proceeded with retention of : configuration. (2R,3S)-[3-H-2(1)] Phenylalanine reacted with (S)-phenylalanine ammonia-lyase to give [3-H-2(1)] -trans-cinnamic acid, with 92% deuterium incorporation; while the (2R,3R) -stereoisomer of the deuteriated phenylalanine gave [3-H-2(1)] -trans-cinnamic acid with 27% deuterium incorporation. These results indicate that reaction of (R)-phenylalanine with the enzyme involves mainly loss of the 3-pro-R hydrogen and ammonia, in an antiperiplanar elimination process analogous to that previously reported for (S)-phenylalanine,while a minor pathway for reaction of :(R)-phenylalanine is either isomerization to (S)-phenylalanine; before elimination, or synperiplanar elimination.

  DOI：

  10.1039/p19940003545

文献信息

• Synthesis of each stereoisomer of [3-2H1]phenylalanine and evaluation of the stereochemical course of the reaction of (R)-phenylalanine with (S)-phenylalanine ammonia-lyase
  作者：Christopher J. Easton、Craig A. Hutton

  DOI：10.1039/p19940003545

  日期：——

  The four stereoisomers of [3-H-2(1)] phenylalanine have been prepared. each as a single enantiomer in ca. 98% diastereoisomeric excess and with ca. 99% deuterium incorporation, by Side-chain bromination of phenylalanine derivatives, followed by deuteriolysis of each of the diastereoisomeric product bromides with deuterium over 5% palladium-on-carbon. The latter reactions, proceeded with retention of : configuration. (2R,3S)-[3-H-2(1)] Phenylalanine reacted with (S)-phenylalanine ammonia-lyase to give [3-H-2(1)] -trans-cinnamic acid, with 92% deuterium incorporation; while the (2R,3R) -stereoisomer of the deuteriated phenylalanine gave [3-H-2(1)] -trans-cinnamic acid with 27% deuterium incorporation. These results indicate that reaction of (R)-phenylalanine with the enzyme involves mainly loss of the 3-pro-R hydrogen and ammonia, in an antiperiplanar elimination process analogous to that previously reported for (S)-phenylalanine,while a minor pathway for reaction of :(R)-phenylalanine is either isomerization to (S)-phenylalanine; before elimination, or synperiplanar elimination.