N-(1-deoxy-D-fructos-1-yl)-L-tyrosine | 87251-89-6

• 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: N-(1-deoxy-D-fructos-1-yl)-L-tyrosine
• 英文别名: (2S)-3-(4-hydroxyphenyl)-2-[[(2R,3S,4R,5R)-2,3,4,5-tetrahydroxyoxan-2-yl]methylamino]propanoic acid
• CAS: 87251-89-6
• 化学式: C₁₅H₂₁NO₈
• 分子量: 343.334
• InChiKey: FWMCIFGEKHMBGO-IHWVXMPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.22
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  159.71
• 氢给体数：
  7.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  (S)-3-(4-Hydroxy-phenyl)-2-[((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl)-amino]-propionic acid 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 24.0h， 以65%的产率得到N-(1-deoxy-D-fructos-1-yl)-L-tyrosine
  参考文献：
  名称：

  Synthesis and¹³C NMR investigation of novel Amadori compounds (1-amino-1-deoxy-D-fructose derivatives) related to the opioid peptide, leucine–enkephalin

  摘要：

  The N-(1-deoxy-D-fructos-1-yl) derivatives (Amadori compounds) of the endogenous opioid pentapeptide, leucine-enkephalin (11), leucine-enkephalin methyl ester (12) and of structurally related peptides (9, 10) are synthesized. The equilibrium compositions of the prepared Amadori compounds 9-12 in D2O and [H-2(6)]DMSO are determined using C-13 NMR spectroscopy. In water, the beta-pyranose, a-furanose and beta-furanose forms are detected, the beta-pyranose tautomer being the most abundant at equilibrium (67-75%). The alpha-pyranose form and open-chain keto form are not detected. In dimethyl sulfoxide, the equilibrium compositions of 9-12 are markedly shifted towards a higher proportion of furanose forms, amounting to two-thirds of the mixture. In addition to the alpha- and beta-furanoses and beta-pyranose tautomers, DMSO solutions of compounds 9-12 contain at equilibrium a relatively high proportion of the acyclic hydrate (gem-diol) form (ca. 10%).

  DOI：

  10.1039/p29960000789

文献信息

• An Unusual Decarboxylative Maillard Reaction between <scp>l</scp>-DOPA and <scp>d</scp>-Glucose under Biomimetic Conditions:  Factors Governing Competition with Pictet−Spengler Condensation
  作者：Paola Manini、Marco d'Ischi、Giuseppe Prota

  DOI：10.1021/jo010078d

  日期：2001.7.1

  37 degrees C, the tyrosine metabolite L-3,4-dihydroxyphenylalanine (L-DOPA) reacts smoothly with D-glucose to afford, besides diastereoisomeric tetrahydroisoquinolines 1 and 2 by Pictet-Spengler condensation, a main product shown to be the unexpected decarboxylated Amadori compound N-(1-deoxy-D-fructos-1-yl)-dopamine (3). Under similar conditions, dopamine gave only tetrahydroisoquinoline products 4

  在pH 7.4和37摄氏度，pH 7.4的0.1 M磷酸盐缓冲液中，酪氨酸代谢物L-3,4-二羟基苯丙氨酸（L-DOPA）与D-葡萄糖平稳反应，从而得到非对映异构的四氢异喹啉1和2，通过Pictet-Spengler缩合反应得到主要产物显示为出乎意料的脱羧Amadori化合物N-（1-脱氧-D-果糖-1-基）-多巴胺（3）。在相似的条件下，多巴胺仅产生四氢异喹啉产物4和5，而L-酪氨酸仅产生典型的Amadori化合物6。Fe（3+）和Cu（2+）离子在帕金森氏黑质中积累相对较高，两者抑制了3的形成。Cu（2+）离子也同样抑制了1和2的形成，而Fe（3+）离子增加了1和2的产率。3的形成与最初的席夫碱加合物的简单脱羧不相容，而是涉及由儿茶酚环辅助的假定的恶唑烷-5-酮中间体的脱羧分解。这些结果报道了在仿生条件下氨基酸和碳水化合物之间的首次脱羧美拉德反应，并突出了过渡金属离子在与Pictet-Spengler缩合竞争中的关键作用。
• Electrospray positive ionization tandem mass spectrometry of Amadori compounds
  作者：Jun Wang、Yi-Min Lu、Bai-Zhan Liu、He-Yong He

  DOI：10.1002/jms.1290

  日期：2008.2