(3-S)-3-Amino-2-hydroxybutanoic acid | 565-81-1

• 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: (3-S)-3-Amino-2-hydroxybutanoic acid
• 英文别名: β-amino-α-hidroxybutyric acid；3-amino-2-hydroxybutanoic acid；3-amino-2-hydroxybutyric acid；Isothreonine；3-amino-2-hydroxy-butyric acid；α-Oxy-β-amino-propan-α-carbonsaeure；Butanoic acid, 3-amino-2-hydroxy-
• CAS: 565-81-1
• 化学式: C₄H₉NO₃
• 分子量: 119.12
• InChiKey: QTRAXZHIRXYYPP-UHFFFAOYSA-N

物化性质

• 溶解度：
  0.44 M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-S)-3-Amino-2-hydroxybutanoic acid 以 水 为溶剂， 生成 L-丙氨酸
  参考文献：
  名称：

  OXIDATIVE DEGRADATION OF HYDROXY AMINO ACIDS BY CONTACT GLOW DISCHARGE ELECTROLYSIS

  摘要：

  为了证实接触辉光放电电解法氧化降解 β- 和 γ- 氨基酸的反应途径，对几种羟基氨基酸进行了氧化降解。结果表明，羟基氨基酸的反应产物支持了 β- 和 γ- 氨基酸氧化降解经过羟基氨基酸的假设。

  DOI：

  10.1246/cl.1980.1545
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氨 作用下， 生成 (3-S)-3-Amino-2-hydroxybutanoic acid
  参考文献：
  名称：

  Melikow, Justus Liebigs Annalen der Chemie, 1886, vol. 234, p. 207

  摘要：

  DOI：

文献信息

• Efficient syntheses of enantiomerically pure L and D-allothreonines and (S) and (R) isoserines
  作者：Dominique Pons、Monique Savignac、Jean-Pierre Genet

  DOI：10.1016/s0040-4039(00)97795-5

  日期：1990.1

  Both enantiomers of (S) and (R) isoserine as well (D) and (L) allothreonine are prepared optically pure in three steps by asymmetric Sharpless epoxidation of crotyl and allylic alcohols into - followed by an improved RuCl3/NaIO4/water oxidation procedure to low molecular weight glycidic acids and epoxide opening by ammonia with (20 – 33%) overall yields.

  （S）和（R）异丝氨酸的对映体以及（D）和（L）别甲苏氨酸都是通过三步光学纯化的，方法是将巴豆基和烯丙醇的不对称Sharpless环氧化为-然后是经过改进的RuCl 3 / NaIO 4 /水氧化过程可制得低分子量的缩水甘油酸，氨气可将环氧化合物打开，总收率为（20％-33％）。
• OXIDATIVE DEGRADATION OF β- AND γ-AMINO ACIDS BY CONTACT GLOW DISCHARGE ELECTROLYSIS
  作者：Kaoru Harada、Jun-ichi Terasawa

  DOI：10.1246/cl.1980.441

  日期：1980.4.5

  The degradation of β- and γ-amino acids in aqueous solutions by contact glow discharge electrolysis(CGDE) was studied. It was found that the reaction is actually a stepwise oxidative degradation by hydroxyl radical produced by CGDE.

  研究了接触辉光放电电解法（CGDE）降解水溶液中的β-和γ-氨基酸。研究发现，该反应实际上是由 CGDE 产生的羟基自由基逐步氧化降解的过程。
• Synthesis of peptidyl fluoromethyl ketones and peptidyl .alpha.-keto esters as inhibitors of porcine pancreatic elastase, human neutrophil elastase, and rat and human neutrophil cathepsin G
  作者：Norton P. Peet、Joseph P. Burkhart、Michael R. Angelastro、Eugene L. Giroux、Shujaath Mehdi、Philippe Bey、Michael Kolb、Bernhard Neises、Daniel Schirlin

  DOI：10.1021/jm00163a063

  日期：1990.1

  Comparison of MeO-Suc-Val-Pro-Phe-CO2Me (29) and MeO-Suc-Ala-Ala-Pro-Phe- CO2Me (25) with their corresponding trifluoromethyl ketones 9a and 9b, respectively, in rat and human neutrophil cathepsin G assays showed the alpha-keto esters to be more potent inhibitors. Likewise, Ac-Pro-Ala-Pro-Ala-CO2Me (21) was more potent than its corresponding trifluoromethyl ketone (9c) in both porcine pancreatic elastase and human neutrophil elastase assays. Within a set of Ala-Ala-Pro-Val-CF3 elastase inhibitors, the carbobenzyloxy (Cbz) N-protecting group conferred greater potency as a P5 site recognition unit for elastase than did dansyl, methoxysuccinyl, or tert-butyloxycarbonyl. Initial inhibition of elastase was greater when trifluoromethyl ketone 9f was added from a stock solution of dimethyl sulfoxide than when it had been buffer-equilibrated prior to assay, which suggests that the nonhydrated ketone is the more effective form of the inhibitor. The most potent elastase inhibitor we report is Na-(Ad-SO2)-N epsilon-(MeO-Suc)Lys-Pro-Val-CF3 (16) which has a Ki of 0.58 nM.
• Neuberg, Biochemische Zeitschrift, 1906, vol. 1, p. 290
  作者：Neuberg

  DOI：——

  日期：——
• PEET, NORTON P.;BURKHART, JOSEPH P.;ANGELASTRO, MICHAEL R.;GIROUX, EUGENE+, J. MED. CHEM., 33,(1990) N, C. 394-407
  作者：PEET, NORTON P.、BURKHART, JOSEPH P.、ANGELASTRO, MICHAEL R.、GIROUX, EUGENE+

  DOI：——

  日期：——