(2R,3S)-2-氨基-3-羟基-戊酸 | 104531-21-7

• 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: (2R,3S)-2-氨基-3-羟基-戊酸
• 英文名称: (2R,3S)-3-hydroxy norvaline
• 英文别名: (+)-(2R,3S)-3-Ethylserine；(2R,3S)-2-azaniumyl-3-hydroxypentanoate
• CAS: 104531-21-7
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: LGVJIYCMHMKTPB-IUYQGCFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-氨基-3-羟基-戊酸 以64%的产率得到
  参考文献：
  名称：

  PANSARE, SUNIL V.;VEDERAS, JOHN C., J. ORG. CHEM., 54,(1989) N0, C. 2311-2316

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,5R,1'S)-1-benzoyl-2-tert-butyl-5-(1'-hydroxypropyl)-3-methylimidazolidin-4-one 在 盐酸 作用下， 反应 22.0h， 以91%的产率得到(2R,3S)-2-氨基-3-羟基-戊酸
  参考文献：
  名称：

  Synthesis and reactivity of .beta.-lactones derived from L-threonine and related amino acids

  摘要：

  DOI：

  10.1021/jo00271a013

文献信息

• Optical Resolution of β-Hydroxynorvaline
  作者：Masaki Yamada、Kenji Okawa

  DOI：10.1246/bcsj.58.2889

  日期：1985.10

  β-Hydroxy-Dl-norvaline(HyNva) was successfully separated into its diastereoisorners by fractional crystallization from 2-propanol as p-toluenesulfonic acid(TsOH) salts. The two racemic diastereoisorners were resolved into four stereoisomers by Vogler’s method, using diastereomers of the N-benzyloxycarbonyl Dl-amino acid and l-tyrosine hydrazide.

  β-羟基-Dl-诺瓦林（HyNva）成功地通过从2-丙醇中分步结晶分离为其不同的非对映体。利用Vogler的方法，这两个外消旋非对映体又被分解为四种立体异构体，使用了N-苄氧基羧基Dl-氨基酸和l-酪氨酸肼的非对映体。
• Asymmetric Synthesis of α-Amino-β-hydroxy Acids Using a Chiral Pyridoxal-Like Pyridinophane–Zinc Complex as an Enzyme Mimic; Scope and Limitation
  作者：Makoto Ando、Jun Watanabe、Hiroyoshi Kuzuhara

  DOI：10.1246/bcsj.63.88

  日期：1990.1

  A chelate complex (4) with high homogeneity was precipitated upon stirring a mixture of zinc(II) ion and a Schiff base produced from glycine and (R)- or (S)-15-formyl-14-hydroxy-2,8-dithia[9](2,5)pyridinophane, chiral pyridoxal-like pyridinophane. A four-coordinated zinc chelate complex was newly proposed as the structure of 4. Aldol condensations between 4 and several aldehydes were attempted at pH

  在搅拌锌（II）离子和由甘氨酸和（R）-或（S）-15-甲酰基-14-羟基-2,8-产生的席夫碱的混合物时，沉淀出具有高均匀性的螯合物（4） dithia[9](2,5)pyridinophane，手性吡哆醛样吡啶酚。新提出了一种四配位的锌螯合物作为 4 的结构。在 pH 10.0 下尝试了 4 和几种醛之间的羟醛缩合。在这些条件下，只有小的直链醛，如乙醛和丙醛，才能与 4 反应，得到相应的 α-氨基-β-羟基酸，对映体过量 27-77%。
• Disubstituted Beta-lactones as Inhibitors of N-Acylethanolamine Acid Amidase (NAAA)
  申请人：The Regents of the University of California

  公开号：US20130281490A1

  公开（公告）日：2013-10-24

  The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.

  本发明提供了一种抑制N-酰乙醇胺酸酰胺酶（NAAA）的化合物和制药组合物。抑制NAAA被认为是一种维持在低浓度下的PEA和OEA的水平的方法，这两种物质是NAAA的底物。本发明还提供了治疗炎症性疾病、疼痛和其他与PEA和OEA浓度降低相关的疾病的方法。
• DISUBSTITUTED BETA-LACTONES AS INHIBITORS OF N-ACYLETHANOLAMINE ACID AMIDASE (NAAA)
  申请人：Fondazione Istituto Italiano Di Tecnologia

  公开号：US20160235707A1

  公开（公告）日：2016-08-18

  The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.

  本发明提供了用于抑制N-乙酰基乙醇胺酸酰化酶（NAAA）的化合物和制药组合物。抑制NAAA被认为是一种维持在PEA和OEA两种NAAA底物的水平在浓度降低的情况下的方法。本发明还提供了用于治疗炎症性疾病和疼痛以及其他与PEA和OEA水平下降相关的疾病的方法。
• Disubstituted beta-lactones as inhibitors of N-acylethanolamine acid amidase (NAAA)
  申请人：The Regents of the University of California

  公开号：US09353075B2

  公开（公告）日：2016-05-31

  The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.

  本发明提供了抑制N-酰基乙醇胺酸酰胺酶（NAAA）的化合物和制药组合物。抑制NAAA被认为是一种维持在浓度降低的情况下的棕榈酰乙醇胺（PEA）和油酰乙醇胺（OEA）水平的方法，这两种物质是NAAA的底物。本发明还提供了治疗炎症性疾病和疼痛，以及其他与PEA和OEA浓度降低相关的疾病的方法。

表征谱图