L-aspartyl-D,L-2-furylglycine 2,5-dimethylcyclopentyl ester | 112395-42-3

• 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,L-2-furylglycine 2,5-dimethylcyclopentyl ester
• 英文别名: (3S)-3-azaniumyl-4-[[2-(2,5-dimethylcyclopentyl)oxy-1-(furan-2-yl)-2-oxoethyl]amino]-4-oxobutanoate
• CAS: 112395-42-3
• 化学式: C₁₇H₂₄N₂O₆
• 分子量: 352.387
• InChiKey: SEEQMBCQWWEPCO-URFHGSOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-氨基-2-呋喃乙酸 在 Pd/C poisoned with quinoline 4-二甲氨基吡啶 、 氢气 、 sodium carbonate 、 一水合肼 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， -65.0~25.0 ℃ 、344.73 kPa 条件下， 反应 11.33h， 生成 L-aspartyl-D,L-2-furylglycine 2,5-dimethylcyclopentyl ester
  参考文献：
  名称：

  High-potency dipeptide sweeteners. 2. L-Aspartylfuryl-, thienyl-, and imidazolylglycine esters

  摘要：

  Eight L-aspartyl dipeptides derived from heterocyclic glycine esters were prepared and evaluated as sweeteners. The fenchyl esters of L-aspartyl-2-furyl-, 2- and 3-thienyl-, and imidazolylglycine were all potently sweet with the D-2-furylglycine (+)-beta-fenchyl ester being the most potent at 16,500 times the potency of sucrose. The requirement for a planar heterocyclic group directly attached to the glycine carbon atom was demonstrated by the observation that the tetrahydrofuryl and beta-thienylalanine fenchyl esters were not sweet. The heteroaromatic glycine esters join the phenylglycine esters as a novel class of dipeptide sweeteners with very high potency.

  DOI：

  10.1021/jm00168a022

文献信息

• JANUSZ, J. M.;YOUNG, P. A.;BLUM, R. B.;RILEY, C. M., J. MED. CHEM., 33,(1990) N, C. 1676-1682
  作者：JANUSZ, J. M.、YOUNG, P. A.、BLUM, R. B.、RILEY, C. M.

  DOI：——

  日期：——
• High-potency dipeptide sweeteners. 2. L-Aspartylfuryl-, thienyl-, and imidazolylglycine esters
  作者：John M. Janusz、P. A. Young、R. B. Blum、C. M. Riley

  DOI：10.1021/jm00168a022

  日期：1990.6

  Eight L-aspartyl dipeptides derived from heterocyclic glycine esters were prepared and evaluated as sweeteners. The fenchyl esters of L-aspartyl-2-furyl-, 2- and 3-thienyl-, and imidazolylglycine were all potently sweet with the D-2-furylglycine (+)-beta-fenchyl ester being the most potent at 16,500 times the potency of sucrose. The requirement for a planar heterocyclic group directly attached to the glycine carbon atom was demonstrated by the observation that the tetrahydrofuryl and beta-thienylalanine fenchyl esters were not sweet. The heteroaromatic glycine esters join the phenylglycine esters as a novel class of dipeptide sweeteners with very high potency.