(2S,3s)-3-氨基-2-羟基-5-甲基己酸 | 73397-20-3

• 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: (2S,3s)-3-氨基-2-羟基-5-甲基己酸
• 英文名称: (2S,3S)-3-Amino-2-hydroxy-5-methylhexanoic Acid
• 英文别名: 3(S)-amino-2(S)-hydroxy-5-methylhexanoic acid；(2S,3S)-3-azaniumyl-2-hydroxy-5-methylhexanoate
• CAS: 73397-20-3
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: GZLMFCWSEKVVGO-WDSKDSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  光气 、 (2S,3s)-3-氨基-2-羟基-5-甲基己酸 在 氢氧化钾 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以36%的产率得到(4S,5S)-4-(2-methylpropyl)-2-oxo-1,3-oxazolidine-5-carboxylic acid
  参考文献：
  名称：

  Renin inhibitors. Substitution of the leucyl residues of Leu-Leu-Val-Phe-OCH3 with 3-amino-2-hydroxy-5-methylhexanoic acid

  摘要：

  The 2S,3S and 2R,3S diastereoisomers of the hydroxy amino acid 3-amino-2-hydroxy-5-methylhexanoic acid (AHMHA) were synthesized and substituted for the leucyl residues of Leu-Leu-Val-Phe-OCH3 to yield the following analogues: AHMHA-Leu-Val-Phe-OCH3, AHMHA-Val-Phe-OCH3, and Leu-AHMHA-Val-Phe-OCH3. These analogues were tested in vitro for their ability to inhibit human amniotic renin. All of the analogues were found to inhibit renin to some extent with inhibitory constants in the range of 10(-3) to 10(-4) M. The analogues AHMHA-Leu-Val-Phe-OCH3 and AHMHA-Val-Phe-OCH3 exhibited competitive inhibition when the 2S,3S isomer of AHMHA was employed and noncompetitive kinetics when the 2R,3S isomer of AHMHA was used. For the Leu-AHMHA-Val-Phe-OCH3 analogues, competitive kinetics were observed regardless of the isomer of AHMHA employed. These latter analogues also proved to be the most active in the above series.

  DOI：

  10.1021/jm00347a024
• 作为产物：
  描述：

  2-蝶啶胺,4,7-二甲基- 在 sodium hydroxide 、 水 、 三乙胺 、 三氟乙酸 作用下， 生成 (2S,3s)-3-氨基-2-羟基-5-甲基己酸
  参考文献：
  名称：

  Synthesis of (2S,3R)-3-amino-2-hydroxy-5-methylhexanoic acid derivatives. Application to the synthesis of amastatin, an inhibitor of aminopeptidases

  摘要：

  DOI：

  10.1021/jo01300a004

文献信息

• Synthesis and structure-activity relationships of amastatin analogues, inhibitors of aminopeptidase A.
  作者：Hiroyasu TOBE、Hajime MORISHIMA、Takaaki AOYAGI、Hamao UMEZAWA、Kunio ISHIKI、Kenji NAKAMURA、Takeo YOSHIOKA、Yasutaka SHIMAUCHI、Taiji INUI

  DOI：10.1271/bbb1961.46.1865

  日期：——

  Stereoisomers and analogues of amastatin, [(2S, 3R)-3-amino-2-hydroxy-5-methylhexanoyl]-L-Val-L-Val-L-Asp, were synthesized and their inhibitory activities towards aminopeptidase A (AP-A) and other arylamidases tested. Among the four stereoisomers of a new amino acid residue in amastatin, the 2S stereoisomers exhibited strong activity. In a series of compounds in which the C-terminal amino acid of amastatin was substituted by other amino acids, the one containing Asp or Glu showed the strongest activity towards AP-A. In a series of compounds in which the second or third residue from the amino terminal of amastatin was substituted by other amino acids, the one containing hydrophobic amino acids showed strong activity. In the study of the relationship of the length of the peptide chain and inhibitory activity, the activity towards AP-A was seen to increase until the length of the peptide reached that of a tetrapeptide.

  阿马司他（(2S,3R)-3-氨基-2-羟基-5-甲基己酰基-L-缬氨酰-L-缬氨酰-L-天冬氨酸）的立体异构体和类似物被合成，并测试了它们对氨基肽酶A（AP-A）和其他芳基酰胺酶的抑制活性。在阿马司他中一个新的氨基酸残基的四种立体异构体中，2S立体异构体表现出强烈的活性。在一系列将阿马司他C端氨基酸替换为其他氨基酸的化合物中，含有Asp或Glu的化合物对AP-A显示出最强的活性。在一系列将阿马司他从氨基端开始的第二个或第三个残基替换为其他氨基酸的化合物中，含有疏水氨基酸的化合物表现出强烈的活性。在研究肽链长度与抑制活性关系的研究中，随着肽链长度达到四肽水平，对AP-A的活性逐渐增加。
• Acceleration of Mycobacterium growth
  申请人：ST GEORGE'S HOSPITAL MEDICAL SCHOOL

  公开号：US10633630B2

  公开（公告）日：2020-04-28

  The invention is in the field of growth of Mycobacteria. In particular, agents have been identified which enhance the growth of Mycobacterial species, which are naturally slow-growing. Such agents can therefore be used in the identification of Mycobacteria and in the diagnosis of Mycobacterial infections.

  本发明属于分枝杆菌生长领域。特别是，已经发现了能促进自然生长缓慢的分枝杆菌生长的制剂。因此，这些制剂可用于分枝杆菌的鉴定和分枝杆菌感染的诊断。
• TAXANE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF
  申请人：INDENA S.p.A.

  公开号：EP1192162B1

  公开（公告）日：2004-09-29
• Stereoselective cyanation of chiral α-amino aldehydes by reaction with Nagata's reagent: a route to enantiopure β-amino-α-hydroxy acids
  作者：José M. Andrés、Marı́a A. Martı́nez、Rafael Pedrosa、Alfonso Pérez-Encabo

  DOI：10.1016/s0957-4166(01)00044-1

  日期：2001.2

  Chiral alpha -dibenzylamino aldehydes react with diethylaluminum cyanide leading to anti-beta -dibenzylamino-alpha -hydroxy-cyanides as the major diastereoisomers in good yields and diastereomeric excesses. Hydrolysis of the nitrile derivatives allows the synthesis of enantiopure beta -amino-alpha -hydroxy acids. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of (2S,3R)-3-amino-2-hydroxy-5-methylhexanoic acid: bridging effect of potassium fluoride
  作者：A. Solladie-Cavallo、N. Khiar

  DOI：10.1021/jo00302a050

  日期：1990.7