Homoisoleucine | 3570-21-6

• 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: Homoisoleucine
• 英文别名: Tetrahydrohypoglycin A；β--alanin；2-amino-4-methyl-hexanoic acid；2-Amino-4-methyl-hexansaeure；4-methyl-norleucine；2-Amino-4-methylhexanoic acid
• CAS: 3570-21-6
• 化学式: C₇H₁₅NO₂
• mdl: MFCD16681302
• 分子量: 145.202
• InChiKey: MBZXSJWDBIIBLL-UHFFFAOYSA-N

物化性质

• 沸点：
  243.4±23.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 Homoisoleucine 在 氢气 作用下， 生成 Homoisoleucine methyl ester
  参考文献：
  名称：

  Seven More Microcystins from Homer Lake Cells: Application of the General Method for Structure Assignment of Peptides Containing .alpha.,.beta.-Dehydroamino Acid Unit(s)

  摘要：

  Larger scale isolation of microcystins, cyclic heptapeptide hepatotoxins, from a water bloom of Microcystis spp. collected from Homer Lake (Illinois) gave the previously reported 1-5, additional quantities of [L-MeSer(7)]microcystin-LR (6), and microcystin-(H-4)YR [8, (H-4)Y = 1',2',3',4'-tetrahydrotyrosine], which were previously isolated in insufficient amounts to complete the structure assignment, and seven more microcystins, 9-15. A general method for assigning the structures of cyclic peptides containing alpha,beta-unsaturated amino acid unit(s) developed with nodularin, a cyclic pentapeptide hepatotoxin, was applied to confirm the previously assigned structures of 1-5 and to assign the structures of [D-Asp(3)]microcystin-LR (9) and the. new microcystin-HilR (10, Hil = homoisoleucine). The method consists of linearization of a cyclic molecule by a one-pot reaction sequence (ozonolysis followed by NaBH4 reduction) and tandem FARMS (FABMS/CID/MS) analysis of the product (linear peptide). A new microcystin, 11, was assigned the structure [L-MeLan(7)]microcystin-LR (MeLan = N-methyllanthionine) and synthesized from 1 and L-Cys. Four linear peptides 12-15, which are reasonable biogenetic precursors of the cyclic compounds, were also assigned structures based on their FABMS/CID/MS data.

  DOI：

  10.1021/jo00117a017
• 作为产物：
  描述：

  2-甲基-丁烯 在 platinum(IV) oxide N-溴代丁二酰亚胺(NBS) 、 氢气 、 过氧化苯甲酰 作用下， 以 溶剂黄146 、 苯 为溶剂， 生成 Homoisoleucine
  参考文献：
  名称：

  Heyns,K. et al., Chemische Berichte, 1961, vol. 94, p. 1015 - 1025

  摘要：

  DOI：

文献信息

• MODULATORS OF SESTRIN-GATOR2 INTERACTION AND USES THEREOF
  申请人：Navitor Pharmaceuticals, Inc.

  公开号：US20170114080A1

  公开（公告）日：2017-04-27

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用相同的方法。
• Inhibitors of hepatitis C virus NS3 protease
  申请人：——

  公开号：US20020065248A1

  公开（公告）日：2002-05-30

  The present invention relates to compounds of Formula (I): 1 wherein A 1 is methylene, ethylene or propylene group and A 2 is N or CR 5 , or stereoisomeric forms, stereoisomeric mixtures, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of HCV NS3 protease, and to pharmaceutical compositions and diagnostic kits comprising the same, and methods of using the same for treating viral infection or as an assay standard or reagent.

  本发明涉及化合物的结构公式（I）：其中A1为亚甲基、乙烯基或丙烯基，A2为N或CR5，或其立体异构体形式、立体异构体混合物或药用盐形式，用作HCV NS3蛋白酶的抑制剂，以及包含相同化合物的药物组合物和诊断试剂盒，以及用于治疗病毒感染或作为测定标准或试剂的方法。
• Cytotoxic Microcolin Lipopeptides from the Marine Cyanobacterium <i>Moorea producens</i>
  作者：Hao-Bing Yu、Evgenia Glukhov、Yueying Li、Arihiro Iwasaki、Lena Gerwick、Pieter C. Dorrestein、Bing-Hua Jiao、William H. Gerwick

  DOI：10.1021/acs.jnatprod.9b00549

  日期：2019.9.27

  Structurally unusual amino acid units, 4-methyl-2-(methylamino)pent-3-enoic (Mpe) acid and 2-amino-4-methylhexanoic acid (N-Me-homoisoleucine), in compounds 1-3 and 8, respectively, are rare residues in naturally occurring peptides. These metabolites showed significant cytotoxic activity against H-460 human lung cancer cells with IC50 values ranging from 6 nM to 5.0 μM. The variations in structure and attendant

  使用生物测定指导和LC-MS / MS分子网络方法，从海洋蓝藻莫雷阿氏酵母菌中分离出九种新的线性脂肽，微菌素EM（1-9），以及四种已知的相关化合物，微菌素AD（10-13）。小分子树素AD（10-13）的催化加氢分别产生了两种已知的化合物3,4-二氢小分子树素A和B（14、15）和两种新的衍生物3,4-二氢小分子树素C和D（16、17）。这些新化合物的结构通过光谱学和先进的Marfey分析相结合来确定。结构异常的氨基酸单元，分别在化合物1-3和8中，分别为4-甲基-2-（甲基氨基）戊-3-烯酸（Mpe）和2-氨基-4-甲基己酸（N-Me-高苏氨酸）在天然肽中是稀有残基。这些代谢物显示出对H-460人肺癌细胞的显着细胞毒活性，IC50值范围为6 nM至5.0μM。结构的变化和伴随的生物学活性提供了关于脂肽的微柱蛋白类的结构-活性关系的新见解。
• Peptide inhibitors of hepatitis C virus NS3 protein
  申请人：——

  公开号：US20020177725A1

  公开（公告）日：2002-11-28

  This invention relates to a novel class of peptides having the Formula (I): 1 Which are useful as serine protease inhibitors, and more particularly as Hepatitis C virus(HCV) NS3 protease inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of using the same in the treatment of HCV infection.

  本发明涉及一类新型肽的公式(I)：1，其作为丝氨酸蛋白酶抑制剂具有用途，更具体地作为丙型肝炎病毒（HCV）NS3蛋白酶抑制剂。本发明还涉及包含这些化合物的制药组合物以及使用它们治疗HCV感染的方法。
• [EN] ALPHA-KETOAMIDE INHIBITORS OF HEPATITIS C VIRUS NS3 PROTEASE<br/>[FR] INHIBITEURS D'ALPHA-CETOAMIDES DE LA PROTEASE NS3 DU VIRUS DE L'HEPATITE C
  申请人：DU PONT PHARM CO

  公开号：WO2001040262A1

  公开（公告）日：2001-06-07

  The present invention relates to ketoamide and ketoester compounds of Formula (I): where W is -NH- or -O-, or stereoisomeric forms, stereoisomeric mixtures, or pharmaceutically acceptable salt forms thereof, which are useful as inhibitors of HCV NS3 protease, and to pharmaceutical compositions and diagnostic kits comprising the same, and methods of using the same for treating viral infection or as an assay standard or reagent.

  本发明涉及式(I)的酮酰胺和酮酯化合物：其中W为-NH-或-O-，或其立体异构体、立体异构体混合物或药学上可接受的盐形式，它们可用作HCV NS3蛋白酶的抑制剂，以及包含它们的制药组合物和诊断试剂盒，以及将它们用于治疗病毒感染或作为测定标准或试剂的方法。

表征谱图