D,L-α-neotame

• 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,L-α-neotame
• 英文别名: (3R)-3-(3,3-dimethylbutylazaniumyl)-4-[[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]amino]-4-oxobutanoate
• 化学式: C₂₀H₃₀N₂O₅
• 分子量: 378.469
• InChiKey: HLIAVLHNDJUHFG-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,3-二甲基丁醛 、 (R)-Asp-(S)-PhOMe 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58%的产率得到D,L-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

文献信息

• Neotame: Synthesis, Stereochemistry and Sweetness
  作者：Indra Prakash、Ihab Bishay、Steve Schroeder

  DOI：10.1080/00397919908086610

  日期：1999.12.1

  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.