D,L-4-咪唑基甘氨酸 | 13726-60-8

• 物质功能分类: 医药中间体
• 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: D,L-4-咪唑基甘氨酸
• 英文名称: D,L-4-imidazolylglycine
• 英文别名: α-histidine；2-Amino-2-(1H-imidazol-5-yl)acetic acid
• CAS: 13726-60-8
• 化学式: C₅H₇N₃O₂
• mdl: MFCD21362541
• 分子量: 141.129
• InChiKey: CXGIFAVNSNJADH-UHFFFAOYSA-N

物化性质

• 熔点：
  225 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  465.4±35.0 °C(Predicted)
• 密度：
  1.520±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  92
• 氢给体数：
  3
• 氢受体数：
  4

制备方法与用途

2-氨基-2-(1H-咪唑-5-基)乙酸可用作有机合成中间体及医药中间体，主要应用于实验室研发和化工、医药生产过程。

反应信息

• 作为反应物：
  描述：

  D,L-4-咪唑基甘氨酸 在 盐酸 、 3 A molecular sieve 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 氯仿 、 水 为溶剂， 反应 7.0h， 生成 N-(tert-butoxycarbonyl)-β-tert-butyl-L-aspartyl-D,L-4-imidazolylglycine (-)-α-fenchyl 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
• 作为产物：
  描述：

  3,4-dihydro-1'(3')H-[4,4']biimidazolyl-2,5-dione 在 水 、 barium carbonate 作用下， 反应 72.0h， 以55%的产率得到D,L-4-咪唑基甘氨酸
  参考文献：
  名称：

  Conformationally-restricted amino acid analogues bearing a distal sulfonic acid show selective inhibition of system over the vesicular glutamate transporter

  摘要：

  A panel of amino acid analogs and conformationally-restricted amino acids bearing a sulfonic acid were synthesized and tested for their ability to preferentially inhibit the obligate cysteine-glutamate transporter system x(c)(-) versus the vesicular glutamate transporter (VGLUT). Several promising candidate molecules were identified: R/S-4-[4'-carboxyphenyl]-phenylglycine, a biphenyl substituted analog of 4-carboxyphenylglycine and 2-thiopheneglycine-5-sulfonic acid both of which reduced glutamate uptake at system x(c)(-) by 70-75% while having modest to no effect on glutamate uptake at VGLUT. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.020

文献信息

• Stewart, Biochemical Journal, 1923, vol. 17, p. 130
  作者：Stewart

  DOI：——

  日期：——
• Polyfunctional macroheterocycles. 7. Synthetic enzyme analogs. synthesis of 16- and 22-membered nitrogen and sulfur crown compounds containing exocyclic histamine and histidine fragments and carboxyl groups
  作者：M. G. Voronkov、V. N. Knutov、O. N. Shevko、M. K. Butin

  DOI：10.1007/bf00528648

  日期：1993.1