N-cbz-(2r,3r)-3-氨基-2-羟基-4-苯基丁酸 | 62023-58-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-cbz-(2r,3r)-3-氨基-2-羟基-4-苯基丁酸
• 英文名称: (2R,3R)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid
• 英文别名: (2R,3R)-3-(N-(benzyloxycarbonyl)amino)-2-hydroxy-4-phenylbutanoic acid；Z-(2R,3R)-AHPA；N-Cbz-(2R,3R)-3-amino-2-hydroxy-4-phenylbutyric acid；(2R,3R)-2-hydroxy-4-phenyl-3-(phenylmethoxycarbonylamino)butanoic acid
• CAS: 62023-58-9
• 化学式: C₁₈H₁₉NO₅
• mdl: MFCD00057840
• 分子量: 329.353
• InChiKey: JXJYTERRLRAUSF-HZPDHXFCSA-N

物化性质

• 熔点：
  172-174 °C
• 沸点：
  581.9±50.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-cbz-(2r,3r)-3-氨基-2-羟基-4-苯基丁酸 在 钯 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 Epibestatin
  参考文献：
  名称：

  Synthesis and structure-activity relations of bestatin analogs, inhibitors of aminopeptidase B

  摘要：

  Stereoisomers and analogues of bestatin, [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine, were synthesized and tested for aminopeptidase B and leucine aminopeptidase inhibiting activity. Among the eight stereoisomers, the 2S stereoisomers exhibited strong activity. In a series of compounds in which the L-leucine residue of bestatin was substituted with other amino acids, only the one containing isoleucine showed more activity than bestatin. Norleucine, norvaline, methionine, valine, serine, glutamine, phenylalanine, glutamic acid, proline, and lysine analogues gave, in that order, decreasing activity. Alkyl and phenyl sub stitution for the benzyl group of bestatin decreased the activity markedly. p-Methyl-, p-chloro-, and p-nitrobestatins showed greater activity than bestatin.

  DOI：

  10.1021/jm00214a010
• 作为产物：
  描述：

  N-Cbz-D-苯丙氨醛 在 盐酸 、 sodium hydroxide 、 水 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 505.0h， 生成 N-cbz-(2r,3r)-3-氨基-2-羟基-4-苯基丁酸
  参考文献：
  名称：

  An improved one-pot method for the stereoselective synthesis of the (2S,3R)-3-amino-2-hydroxy acids: key intermediates for bestatin and amastatin

  摘要：

  DOI：

  10.1021/jo00294a047

文献信息

• Tributyltin Cyanide, a Novel Reagent for the Stereoselective Preparation of 3-Amino-2-hydroxy Acids via Cyanohydrin Intermediates
  作者：Rosario Herranz、Julia Castro-Pichel、Teresa García-López

  DOI：10.1055/s-1989-27367

  日期：——

  Reaction of tributyltin cyanide with optically active 2-N-benzyloxyearbonylamino aldehydes 1 gives the corresponding O-tributylstannyl cyanohydrins 2 and 3 stereoselectively. Compounds 2 and 3 are transformed in situ into the methyl 3-N-benzoyloxycarbonyl-amino-2-hydroxy esters 4 and 5, respectively, via the imidate hydrochloride intermediates. Saponification of 4 and 5 provide 3-amino-2-hydroxy acids 6 and 7, respectively, key intermediates in the preparation of Bestatin, Amastatin, and analogues.

  三丁基氰化锡与光学活性2-N-苯甲氧羰基氨基醛1反应立体选择性地得到相应的O-三丁基甲锡烷基氰醇2和3。化合物2和3通过亚氨酸盐酸盐中间体分别原位转化为甲基3-N-苯甲酰氧基羰基-氨基-2-羟基酯4和5。 4和5的皂化分别提供3-氨基-2-羟基酸6和7，它们是制备Bestatin、Amastatin和类似物的关键中间体。
• Novel 3-amino-2-hydroxy acids containing protease inhibitors. Part 1: Synthesis and kinetic characterization as aminopeptidase P inhibitors
  作者：Angela Stöckel-Maschek、Beate Stiebitz、Regine Koelsch、Klaus Neubert

  DOI：10.1016/j.bmc.2005.05.040

  日期：2005.8

  Novel, potent inhibitors of aminopeptidase P, containing a 3-amino-2-hydroxy acid and a proline ora proline analogues, have been prepared. One part of the bestatin-derived inhibitors was found to inhibit APP from Excherichia coli and from rat intestine according to a mixed-type mechanism, with K-i values up to 1.26 mu M. The other compounds. 3-amino-2-hydroxy acyl prolines of a different configuration. inhibit APP competitively, according to a slow-binding mechanism, with K-i values in the nanomolar up to the micromolar range. (c) 2005 Elsevier Ltd. All rights reserved.
• HERRANZ, ROSARIO;CASTRO-PICHEL, JULIA;VINUESA, SOLEDAD;GARCIA-LOPEZ, M. T+, J. CHEM. SOC. CHEM. COMMUN.,(1989) N4, C. 938-939
  作者：HERRANZ, ROSARIO、CASTRO-PICHEL, JULIA、VINUESA, SOLEDAD、GARCIA-LOPEZ, M. T+

  DOI：——

  日期：——
• HERRANZ, ROSARIO;CASTRO-PICHEL, JULIA;VINUESA, SOLEDAD;GARCIA-LOPEZ, M. T+, J. ORG. CHEM., 55,(1990) N, C. 2232-2234
  作者：HERRANZ, ROSARIO、CASTRO-PICHEL, JULIA、VINUESA, SOLEDAD、GARCIA-LOPEZ, M. T+

  DOI：——

  日期：——