4-hydroxyisoleucine

• 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: 4-hydroxyisoleucine
• 英文别名: RSS-HIL；(2R,3S,4S)-2-amino-4-hydroxy-3-methylpentanoic acid；(2R,3S,4S)-4-hydroxyisoleucine；(2R,3S,4S)-2-azaniumyl-4-hydroxy-3-methylpentanoate
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: OSCCDBFHNMXNME-MROZADKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以173 mg的产率得到4-hydroxyisoleucine
  参考文献：
  名称：

  An Organocatalyzed Enantioselective Synthesis of (2S,3R,4S)-4-Hydroxyisoleucine and Its Stereoisomers

  摘要：

  A concise enantioselective total synthesis of (2S,3/2,45)-4-hydroxyisoleucine and its stereoisomers is described. A key feature of this protocol is a catalytic enantioselective mannich reaction that is either anti- or syn-selective as genesis of chirality.

  DOI：

  10.1021/jo100233u

文献信息

• Compounds and compositions for use in the prevention and treatment of obesity and related syndromes
  申请人：Chapal Nicolas

  公开号：US20060223884A1

  公开（公告）日：2006-10-05

  The invention relates to 4-hydroxyisoleucine, isomers, analogs, lactones, salts, and prodrugs thereof, to processes for their preparation, and to pharmaceutical compositions comprising the same. More particularly, the invention relates to the use of those compounds in the prevention and treatment of obesity and related syndromes.

  本发明涉及4-羟基异亮氨酸、其同分异构体、类似物、内酯、盐和前药，以及它们的制备过程，以及包含它们的药物组合物。更具体地说，本发明涉及这些化合物在预防和治疗肥胖及相关综合症中的用途。
• Attempt to simultaneously generate three chiral centers in 4-hydroxyisoleucine with microbial carbonyl reductases
  作者：Makoto Hibi、Koji Takahashi、Junko Kako、Yuuta Wakita、Tomohiro Kodera、Sakayu Shimizu、Kenzo Yokozeki、Jun Ogawa

  DOI：10.1016/j.bmc.2017.06.044

  日期：2018.4

  A panel of microorganisms was screened for selective reduction ability towards a racemic mixture of prochiral 2-amino-3-methyl-4-ketopentanoate (rac-AMKP). Several of the microorganisms tested produced greater than 0.5 mM 4-hydroxyisoleucine (HIL) from rac-AMKP, and the stereoselectivity of HIL formation was found to depend on the taxonomic category to which the microorganism belonged. The enzymes

  筛选一组微生物对前手性2-氨基-3-甲基-4-酮戊酸酯的外消旋混合物的选择性还原能力（rac -AMKP）。测试的几种微生物从rac -AMKP产生大于0.5 mM的4-羟基异亮氨酸（HIL），并且发现HIL形成的立体选择性取决于该微生物所属的分类学类别。负责该AMKP还原活性的酶，鸭AR和Fs的AR，从两个这些微生物的鉴定，出芽短梗霉NBRC 4466和茄病镰刀菌分别TG-2，。三种AMKP还原酶Ap AR，Fs使AR和先前报道的Bt HILDH与rac -AMKP反应，并且每种酶选择性地产生HIL立体异构体的特定组成。这些酶在识别底物AMKP的立体结构和控制HIL产品中的4-羟基构型方面似乎具有不同的特性。
• Compounds and Compositions for Use in the Prevention and Treatment of Disorders of Fat Metabolism and Obesity
  申请人：Jette Lucie

  公开号：US20100048545A1

  公开（公告）日：2010-02-25

  The invention relates to 4-hydroxyisoleucine, isomers, analogs, lactones, salts, and prodrugs thereof, to processes for their preparation, and to pharmaceutical compositions comprising the same. More particularly, the invention relates to the use of those compounds in the prevention and treatment of disorders of fat metabolism and related syndromes. The invention further relates to the use of those compounds in the prevention and treatment of obesity and related syndromes including, but not limited to, the cosmetic treatment of a mammal in order to effect a cosmetically beneficial loss of body weight, and more particularly loss of body fat.

  本发明涉及4-羟基异亮氨酸、其同分异构体、类似物、内酯、盐和前药的制备方法，以及包含这些化合物的药物组合物。更具体地，本发明涉及这些化合物在预防和治疗脂肪代谢紊乱和相关综合症方面的用途。本发明还涉及这些化合物在预防和治疗肥胖和相关综合症方面的用途，包括但不限于美容治疗哺乳动物，以实现对体重，特别是体脂肪的美容有益的减少。
• DIASTEREOISOMERS OF 4-HYDROXYISOLEUCINE AND USES THEREOF
  申请人：Innodia Inc.

  公开号：EP1853552A2

  公开（公告）日：2007-11-14
• COMPOUNDS AND COMPOSITIONS FOR USE IN THE PREVENTION AND TREATMENT OF OBESITY AND RELATED SYNDROMES
  申请人：Innodia Inc.

  公开号：EP1874287A2

  公开（公告）日：2008-01-09