L-alpha-天冬氨酰-D-苯丙氨酸甲酯 | 22839-65-2

• 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
• 中文名称: L-alpha-天冬氨酰-D-苯丙氨酸甲酯
• 英文名称: α-L-aspartyl-D-phenylalanine methyl ester
• 英文别名: L,D-α-aspartame；aspartame；aspartame (LD)；Asp-D-Phe-Methylester；L-alpha-Aspartyl-D-phenylalanine methyl ester；(3S)-3-amino-4-[[(2R)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoic acid
• CAS: 22839-65-2
• 化学式: C₁₄H₁₈N₂O₅
• 分子量: 294.307
• InChiKey: IAOZJIPTCAWIRG-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,3-二甲基丁醛 、 L-alpha-天冬氨酰-D-苯丙氨酸甲酯 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 40.0 ℃ 、275.79 kPa 条件下， 反应 12.0h， 以89.7%的产率得到L,D-α-neotame
  参考文献：
  名称：

  Neotame: Synthesis, Stereochemistry and Sweetness

  摘要：

  Neotame, an alkylated dipeptide consisting of L,L-stereochemistry, is a new high intensity sweetener being developed by the Nutrition and Consumer Products Sector of Monsanto. The three diastereoisomers of neotame, L,D; D,L; and D,D were synthesized and evaluated for sweetness by sensory testing. Only the L,L-isomer was found to be sweet. The three-dimensional structure of the L,L diastereoisomer determined from single-crystal x-ray analysis demonstrates that the compound exists in an "L shaped" conformation, previously proposed for the requirement of the sweetness ability by aspartyl-based dipeptide compounds. The confirmation of neotame in the solid state also demonstrates well-oriented hydrophobic and hydrophilic regions which likely account for the high sweetness intensity of this dipeptide compound.

  DOI：

  10.1080/00397919908086610
• 作为产物：
  描述：

  D-苯丙氨酸甲酯 在 钯 氢气 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 L-alpha-天冬氨酰-D-苯丙氨酸甲酯
  参考文献：
  名称：

  一些二肽的结构-味道关系。

  摘要：

  DOI：

  10.1021/ja01038a046

文献信息

• 一种化合物3，3-二甲基-羟基磺酸钠及其制备 方法和用途
  申请人：柳玉荣

  公开号：CN105585514B

  公开（公告）日：2018-04-17

  本发明提供一种新化合物3，3‑二甲基‑羟基磺酸钠及其制备方法和用途，本发明3，3‑二甲基‑羟基磺酸钠分子式：C6H13NaO4S分子量：204.2结构式：本发明3,3‑二甲基‑羟基磺酸钠可以作为合成纽甜的中间体，用于制备纽甜。其以固体复盐状态存在，性状更为稳定，同时更加利于存储运输。
• Gem-diaminoalkane derived sweeteners
  申请人：CUMBERLAND PACKING CORPORATION

  公开号：EP0128654A2

  公开（公告）日：1984-12-19

  Compounds of the formula: wherein n is 0 or 1, R is lower alkyl (substituted or unsubstituted), R' is H or lower alkyl, and R" is a branched alkyl, alkyl-cycloalkyl, cycloalkyl, polycycloalkyl (poly = 2 or more, fused or non-fused), phenyl or alkyl-substituted phenyl, and physiologically acceptable cationic and acid addition salts thereof, which compounds are potent sweeteners. These derivatives of gem-diaminoalkanes are many times sweeter than sugar and are free from undesirable flavor qualities. Furthermore, they possess an unanticipated high degree of solubility compared with known synthetic sweeteners. In addition, the compounds possess high stability so that they can be used in all types of beverages and in conventional food processing. Sweetening compositions and sweetened edible compositions of these compounds are also provided.

  式中的化合物： 其中 n 为 0 或 1，R 为低级烷基（取代或未取代），R'为 H 或低级烷基，R "为支链烷基、烷基-环烷基、环烷基、多环烷基（多 = 2 或更多，融合或未融合）、苯基或烷基取代的苯基，以及生理上可接受的阳离子盐和酸加成盐，这些化合物是强效甜味剂。这些宝石二氨基烷烃衍生物的甜度比糖高出许多倍，而且没有不良味道。此外，与已知的合成甜味剂相比，它们还具有意想不到的高溶解度。此外，这些化合物还具有很高的稳定性，因此可用于各类饮料和传统的食品加工中。此外，还提供了这些化合物的甜味组合物和甜味食用组合物。
• Process for preparing alpha-L-aspartyl-L-phenylalanine methyl ester
  申请人：DE-BI DERIVATI BIOLOGICI INTERNATIONAL S.p.A.

  公开号：EP0149263A2

  公开（公告）日：1985-07-24

  A process for preparing a-L-aspartyl-L-phenylalanine methyl ester: in which: a) the compound methyl N(a-L-aspartyl)a-aminocinn- amate, protected at the nitrogen, of formula: where R is a protector group at the nitrogen, is subjected to hydrogenation at the olefin bond by means of gaseous hydrogen in the presence of a hydrogenation catalyst, to give the compound of formula: where R has the aforesaid meaning, in the form of a mixture of a-L-aspartyl-L-phenylalanine methyl ester protected at the nitrogen, and α-αL-aspartyl-D-phenylalanine methyl ester protected at the nitrogen; b) the protector group is removed from said a-L-aspartyl-L-phenylalanine and a-L-aspartyl-D-phenylalanine methyl esters protected at the nitrogen; c) the a-L-aspartyl-L-phenylalanine methyl ester is separated and recovered from said deprotection reaction product.

  一种制备 L-天冬氨酰-L-苯丙氨酸甲酯的工艺： 其中 a) N-(a-L-天冬氨酰)-a-氨基辛-氨甲酸甲酯化合物，氮端受保护，其式如下 式中 R 为氮上的保护基，在氢化催化剂存在下，通过气态氢在烯烃键处进行氢化，得到 式中化合物： 其中 R 具有上述含义，以氮保护的 a-L-天冬氨酰-L-苯丙氨酸甲酯和氮保护的 α-α-L-天冬氨酰-D-苯丙氨酸甲酯混合物的形式存在； b) 从所述受氮保护的 a-L-天冬氨酰-L-苯丙氨酸和 a-L-天冬氨酰-D-苯丙氨酸甲酯中去除保护基； c) 从所述脱保护反应产物中分离并回收 a-L-天冬氨酰-L-苯丙氨酸甲酯。
• Novel intermediates useful in the production of gem-diaminoalkane derived sweeteners
  申请人：CUMBERLAND PACKING CORPORATION

  公开号：EP0242896A2

  公开（公告）日：1987-10-28

  The present invention relates to novel intermediates for use in the production of compounds forming the subject matter of parent Application No. 84302978.6 (Publication No. 0128654). Such intermediate compounds comprise 2,2,5,5-tetramethylcyclopentanone 1,2,2,5,5-pentamethylcyclopentanol 1-methytene-2,2,5,5-tetramethylcyclopentane 2,2,5,5-tetra- methyVcyclopentylmethanol 2,2,5,5-tetramethylcyclopentanecarboxylic acid

  本发明涉及用于生产构成母申请第 84302978.6 号（公开号 0128654）主题的化合物的新型中间体。 这类中间体化合物包括 2,2,5,5-四甲基环戊酮 1,2,2,5,5-五甲基环戊醇 1-甲基-2,2,5,5-四甲基环戊烷 2,2,5,5-四甲基环戊基甲醇 2,2,5,5-四甲基环戊烷羧酸
• Process for separation of N-protected alpha-L-aspartyl-L-phenylalanines
  申请人：Ajinomoto Co., Inc.

  公开号：EP0256812A2

  公开（公告）日：1988-02-24

  Disclosed herein is a process for separating N-­protected-α-L-aspartyl-L-phenylalanine, more particularly a process for selectively separating N-protected-α-L-aspartyl-­L-phenylalanine from a solution of N-protected-α-L-aspartyl-­L-phenylalanine containing at least N-protected-α-L-aspartyl-­D-phenylalanine as impurity.

  本文公开了一种分离 N-保护-α-L-天冬氨酰-L-苯丙氨酸的工艺，特别是从至少含有 N-保护-α-L-天冬氨酰-D-苯丙氨酸作为杂质的 N-保护-α-L-天冬氨酰-L-苯丙氨酸溶液中选择性分离 N-保护-α-L-天冬氨酰-L-苯丙氨酸的工艺。