L-aspartyl-D-alanine (R)-α-methylbenzylamide

• 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: L-aspartyl-D-alanine (R)-α-methylbenzylamide
• 英文别名: L-aspartyl-D-alanine-N-(R)-α-methylbenzyl amide；(3S)-3-amino-4-oxo-4-[[(2R)-1-oxo-1-[[(1R)-1-phenylethyl]amino]propan-2-yl]amino]butanoic acid
• 化学式: C₁₅H₂₁N₃O₄
• 分子量: 307.349
• InChiKey: AUYZYZBJTHDDHM-FOGDFJRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(carbobenzyloxy)-β-benzyl-L-aspartyl-D-alanine 在 palladium on activated charcoal N-羟基-5-降冰片烯-2,3-二甲酰亚胺 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 生成 L-aspartyl-D-alanine (R)-α-methylbenzylamide
  参考文献：
  名称：

  Discovery and Synthesis of a New Series of High-Potency L-Aspartyl-D-.alpha.-aminoalkanoyl-(S)-.alpha.-alkylbenzylamide Sweeteners

  摘要：

  A new series of L-aspartyl-D-amino acid amide sweeteners is described in which the amide portion is prepared from an cl-alkyl-substituted benzylamine. These materials show good taste characteristics and are 5 times more stable than aspartame at typical beverage pH (3-4). The most potent member of the series is L-aspartyl-D-alpha-aminobutyric acid (S)-alpha-ethylbenzylamide, having a sweetness potency 2000 times that of a 10% sucrose solution.

  DOI：

  10.1021/jf00056a003

文献信息

• D-alpha-aminoalkanoyl-(S)-N-alpha-alkylbenzyl amides useful as intermediates for artificial sweeteners
  申请人：THE COCA-COLA COMPANY

  公开号：EP0779296A2

  公开（公告）日：1997-06-18

  The present invention relates to D-α-aminoalkanoyl-(S)-N-α-alkylbenzyl amides which are useful as intermediates for preparing artifical sweetener compounds and to methods for preparing these intermediates.

  本发明涉及可用作制备人造甜味剂化合物中间体的 D-α-氨基烷酰基-(S)-N-α-烷基苄基酰胺，以及制备这些中间体的方法。
• US5286509A
  申请人：——

  公开号：US5286509A

  公开（公告）日：1994-02-15
• [EN] NOVEL INTERMEDIATES FOR THE SYNTHESIS OF L-ASPARTYL-D- alpha -AMINOALKANOYL-(S)-N- alpha -ALKYLBENZYL AMIDES USEFUL AS ARTIFICIAL SWEETENERS<br/>[FR] NOUVEAUX INTERMEDIAIRES POUR LA SYNTHESE D'AMIDES DE L-ASPARTYL-D- alpha -AMINOALCANOYL-(S)-N- alpha -ALKYLBENZYLE UTILES EN TANT QU'EDULCORANTS ARTIFICIELS
  申请人：——

  公开号：WO1995017418A2

  公开（公告）日：1995-06-29

  [EN] The present invention relates to chemical compounds that are useful for the preparation of artificial sweetener compounds, in particular, chemical intermediates that are useful for the preparation of L-aspartyl-D- alpha -aminoalkanoyl-(S)-N- alpha -alkylbenzyl amides.
  [FR] L'invention concerne des composés édulcorants artificiels, et plus particulièrement, des intermédiaires chimiques utiles pour la préparation d'amides de L-aspartyl-D- alpha -aminoalcanoyl-(S)-N- alpha -alkylbenzyle.
• US5286509
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery and Synthesis of a New Series of High-Potency L-Aspartyl-D-.alpha.-aminoalkanoyl-(S)-.alpha.-alkylbenzylamide Sweeteners
  作者：James G. Sweeny、Lihong L. D'Angelo、Edith A. Ricks、Guillermo A. Iacobucci

  DOI：10.1021/jf00056a003

  日期：1995.8

  A new series of L-aspartyl-D-amino acid amide sweeteners is described in which the amide portion is prepared from an cl-alkyl-substituted benzylamine. These materials show good taste characteristics and are 5 times more stable than aspartame at typical beverage pH (3-4). The most potent member of the series is L-aspartyl-D-alpha-aminobutyric acid (S)-alpha-ethylbenzylamide, having a sweetness potency 2000 times that of a 10% sucrose solution.