-2(S)-(2-propenyl)glycyl>-(R)-alanine methyl ester | 146364-58-1

• 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: -2(S)-(2-propenyl)glycyl>-(R)-alanine methyl ester
• 英文别名: N--(R)-alaninmethylester；methyl (2R)-2-[[(2S)-2-(2,2,2-trichloroethoxycarbonylamino)pent-4-enoyl]amino]propanoate
• CAS: 146364-58-1
• 化学式: C₁₂H₁₇Cl₃N₂O₅
• 分子量: 375.636
• InChiKey: LGYXIBQPPSXNCP-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  -2(S)-(2-propenyl)glycyl>-(R)-alanine methyl ester 在 4-二甲氨基吡啶 、 三氯化铁 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.0h， 生成 -(S)-α-<5-oxy>-4-pentenoate>>glycyl>-(R)-alanine methyl ester
  参考文献：
  名称：

  Synthesis of modified partial structures of the bacterial cell wall. 1. Lipopeptides containing nonproteinogenic amino acids

  摘要：

  Two stereoisomeric lipopeptides 1 and 2 which can be regarded as modified peptidoglycans have been synthesized by using three different reaction sequences. The ene reaction of the alpha-allylated dipeptide 12 with butyl glyoxylate was used as a key step. The required enantiomerically pure substrates 9, 10, and 23 were obtained by enzymatic hydrolysis of the corresponding racemic alpha-allylated esters. The absolute configuration of both stereoisomers 1 and 2 was assigned by oxidative cleavage of the double bond in 18 and 19 followed by comparison of the esterified degradation products 28 and 29 with samples of authentic configuration, derived from (R)- and (S)-malic acid.

  DOI：

  10.1021/jo00055a022
• 作为产物：
  描述：

  diethyl 2-<<(2,2,2-trichloroethoxy)carbonyl>amino>-2-(2-propenyl)malonate 在 N-甲基吗啉 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 xylene 为溶剂， 反应 48.0h， 生成 -2(S)-(2-propenyl)glycyl>-(R)-alanine methyl ester
  参考文献：
  名称：

  Synthesis of modified partial structures of the bacterial cell wall. 1. Lipopeptides containing nonproteinogenic amino acids

  摘要：

  Two stereoisomeric lipopeptides 1 and 2 which can be regarded as modified peptidoglycans have been synthesized by using three different reaction sequences. The ene reaction of the alpha-allylated dipeptide 12 with butyl glyoxylate was used as a key step. The required enantiomerically pure substrates 9, 10, and 23 were obtained by enzymatic hydrolysis of the corresponding racemic alpha-allylated esters. The absolute configuration of both stereoisomers 1 and 2 was assigned by oxidative cleavage of the double bond in 18 and 19 followed by comparison of the esterified degradation products 28 and 29 with samples of authentic configuration, derived from (R)- and (S)-malic acid.

  DOI：

  10.1021/jo00055a022

文献信息

• Hornich, Elisabeth; Thirring, Klaus; Berner, Heinz, Scientia Pharmaceutica, 1996, vol. 64, # 3-4, p. 463 - 470
  作者：Hornich, Elisabeth、Thirring, Klaus、Berner, Heinz

  DOI：——

  日期：——
• Synthesis of modified partial structures of the bacterial cell wall. 1. Lipopeptides containing nonproteinogenic amino acids
  作者：Helmut Schneider、Gerhard Sigmund、Bettina Schricker、Klaus Thirring、Heinz Berner

  DOI：10.1021/jo00055a022

  日期：1993.1

  Two stereoisomeric lipopeptides 1 and 2 which can be regarded as modified peptidoglycans have been synthesized by using three different reaction sequences. The ene reaction of the alpha-allylated dipeptide 12 with butyl glyoxylate was used as a key step. The required enantiomerically pure substrates 9, 10, and 23 were obtained by enzymatic hydrolysis of the corresponding racemic alpha-allylated esters. The absolute configuration of both stereoisomers 1 and 2 was assigned by oxidative cleavage of the double bond in 18 and 19 followed by comparison of the esterified degradation products 28 and 29 with samples of authentic configuration, derived from (R)- and (S)-malic acid.