L-leucine isobutyl ester | 45082-53-9

• 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: L-leucine isobutyl ester
• 英文别名: L-Leucin-isobutylester；2-methylpropyl (2S)-2-amino-4-methylpentanoate
• CAS: 45082-53-9
• 化学式: C₁₀H₂₁NO₂
• 分子量: 187.282
• InChiKey: MNWYEJOLGOALMX-VIFPVBQESA-N

物化性质

• 沸点：
  227.5±13.0 °C(Predicted)
• 密度：
  0.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  草酰氯 、 L-leucine isobutyl ester 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以26%的产率得到isobutyl (2S)-2-[[2-[[(1S)-1-isobutoxycarbonyl-3-methyl-butyl]amino]-2-oxo-acetyl]amino]-4-methyl-pentanoate
  参考文献：
  名称：

  Synthesis of symmetrical pseudopeptides as potential inhibitors of the human immunodeficiency virus-1 protease

  摘要：

  It is demonstrated that HIV-1 protease is essential for the assembly and infectivity of the acquired immunodeficiency syndrome (AIDS) virus. This protease is an aspartyl protease with a 2-fold symmetry axis. Potential inhibitors were synthesized and consisted of a spacer linking 2 peptidic chains. They had to satisfy the following constraints: a C-2 symmetry axis, a backbone similar to the peptidic substrates, and side-chains filling the subsites S-n...S'(n). The compounds were synthesized via peptidic synthetic methods and evaluated in an enzymatic test with HIV-1 protease. Several compounds displayed an inhibitory activity at 10 mu M. They possessed the spacers CO, CO-CO, CO-CH2-CHOH-CO and the terminal chain Phe-O-iC(4)H(9). However, the structural-variation-based optimization of these different compounds failed and no potent inhibitors were prepared.

  DOI：

  10.1016/0223-5234(94)90025-6
• 作为产物：
  描述：

  2-甲基丙基L-亮氨酸酸酯 在 L-酒石酸 作用下， 生成 L-leucine isobutyl ester
  参考文献：
  名称：

  Langenbeck; Zimmermann, Chemische Berichte, 1951, vol. 84, p. 524

  摘要：

  DOI：

文献信息

• [EN] MERCAPTOSULFIDE METALLOPROTEINASE INHIBITORS<br/>[FR] MERCAPTOSULFURES INHIBITEURS DE LA METALLOPROTEINASE MATRICE
  申请人：FLORIDA STATE UNIVERSITY

  公开号：WO1995009833A1

  公开（公告）日：1995-04-13

  (EN) Novel mercaptosulfide matrix metalloproteinase inhibitors of formula (I), wherein n is 0 or 1; R1 is selected from the group consisting of hydrogen, lower alkyl, amino lower alkyl, carbamoyl lower alkyl, PhtN (lower alkyl), TsNH (lower alkyl); and R2 is selected from the group consisting of hydrogen, lower alkyl, amino lower alkyl, carbamoyl lower alkyl, PhtN (lower alkyl), TsNH (lower alkyl); or R1 and R2 together are -CH2-CH2-CH2-; R3 is selected from the group consisting of hydrogen, lower alkyl, aralkyl and heteroaralkyl; and R4 is selected from the group consisting of hydrogen, lower alkyl, amino lower-alkyl, guanyl lower-alkyl, imidazoylalkyl, aralkyl and 2-indolylmethyl; and R5 is selected from the group consisting of lower alkyl, aralkyl and -CH(R6)-C(O)NH2, wherein R6 is selected from the group consisting of hydrogen, lower-alkyl, amino lower-alkyl, guanyl lower-alkyl, imidazoylalkyl, hydroxymethyl, 1-hydroxyethyl, mercapto lower-alkyl, and methylthio lower-alkyl; or a pharmaceutically acceptable ester, ether or salt thereof, useful for treating diseases and disease conditions associated with matrix metalloproteinase modulation.(FR) Nouveaux mercaptosulfures inhibiteurs la métalloprotéinase matrice de formule (I) où n représente 0 ou 1; R1 est sélectionné parmi: hydrogène, alkyle inférieur, aminoalkyle inférieur, alkyle inférieur de carbamoyle, PhtN (alkyle inférieur), TsNH (alkyle inférieur); R2 est sélectionné parmi: hydrogène, alkyle inférieur, aminoalkyle inférieur, alkyle inférieur de carbamoyle, PhtN (alkyle inférieur), TsNH (alkyle inférieur); ou R1 et R2 ensemble représentent -CH2-CH2-CH2-: R3 est selectionné parmi: hydrogène, alkyle inférieur, aralkyle et hétéroaralkyle; R4 est sélectionné parmi: hydrogène, alkyle inférieur, aminoalkyle inférieur, alkyle inférieur de guanyle, imidazoylealkyle, aralkyle, et indolyleméthyle 2; R5 est sélectionné parmi: alkyle inférieur, aralkyle, et -CH(R6)-C(0)NH2, dans lequel R6 est sélectionné parmi: hydrogène, alkyle inférieur, aminoalkyle inférieur, alkyle inférieur de guanyle, imidazoylealkyle, hydroxyméthyle, hydroxyéthyle-1, mercaptoalkyle inférieur et méthyléthioalkyle inférieur. Ces nouveaux inhibiteurs ou leurs esters, éthers et sels pharmacocompatibles s'avèrent utiles pour traiter les maladies ou les affections liées à la modulation de la métalloprotéinase matrice.

  （中文）本发明涉及一种公式（I）的新型巯基硫醚基质金属蛋白酶抑制剂，其中n为0或1；R1选自氢、低级烷基、氨基低级烷基、氨基甲酰低级烷基、PhtN（低级烷基）、TsNH（低级烷基）所组成的群；R2选自氢、低级烷基、氨基低级烷基、氨基甲酰低级烷基、PhtN（低级烷基）、TsNH（低级烷基）所组成的群；或R1和R2一起是-CH2-CH2-CH2-；R3选自氢、低级烷基、芳基烷基和杂芳基烷基所组成的群；R4选自氢、低级烷基、氨基低级烷基、胍基低级烷基、咪唑基烷基、芳基烷基和2-吲哚甲基所组成的群；R5选自低级烷基、芳基烷基和-CH（R6）-C（O）NH2所组成的群，其中R6选自氢、低级烷基、氨基低级烷基、胍基低级烷基、咪唑基烷基、羟甲基、1-羟基乙基、巯基低级烷基和甲硫基低级烷基。此外，本发明还涉及其药学上可接受的酯、醚或盐，用于治疗与基质金属蛋白酶调节相关的疾病和疾病状况。
• Process for the separation of L-leucine and L-isoleucine
  申请人：PFW (NEDERLAND) B.V.

  公开号：EP0241094A1

  公开（公告）日：1987-10-14

  The invention relates to a process for the separation of L-leucine and L-isoleucine. The process is carried out by subjecting a mixture of leucine ester, and isoleucine ester (or a mixture of leucine ester, isoleucine ester and valine ester) to an esterase catalyzed hydrolysis resulting in a selective hydrolysis of the leucine ester. The pure L-leucine can be isolated from the reaction mixture by first removing the non-­hydrolyzed esters by extraction with an organic solvent and then crystallizing the L-leucine at its isoelectric point. The recovered L-isoleucine ester is purified by distillation (if necessary), and hydrolyzed go yield pure crystalline L-isoleucine.

  本发明涉及一种分离 L-亮氨酸和 L-异亮氨酸的工艺。该工艺是将亮氨酸酯和异亮氨酸酯的混合物（或亮氨酸酯、异亮氨酸酯和缬氨酸酯的混合物）在酯酶催化下进行水解，从而选择性地水解亮氨酸酯。首先用有机溶剂萃取除去未水解的酯，然后在等电点处结晶 L-亮氨酸，即可从反应混合物中分离出纯净的 L-亮氨酸。回收的 L-异亮氨酸酯可通过蒸馏（如有必要）进行提纯，然后水解得到纯净的 L-异亮氨酸结晶。
• Mild and efficient preparation method for α-acyloxyenamide compounds and use thereof in synthesis of amide and polypeptide
  申请人：Jiangxi Normal University

  公开号：US10836707B2

  公开（公告）日：2020-11-17

  Disclosed are a mild and efficient preparation method for an α-acyloxyenamide compound and a use thereof in the synthesis of an amide and a polypeptide. The α-acyloxyenamide compound is obtained by an addition reaction of a ynamide and a carboxylic acid in dichloromethane under conditions where the temperature is 0° C. to 50° C.; the produced α-acyloxyenamide compound can react with an amine compound to produce an amide or a polypeptide; the two reactions can be carried out step by step, and can also be carried out in one pot. According to the invention, the reaction conditions are mild and no metal catalyst is required; when the carboxylic acid, which has chirality on an alpha site of carboxyl, forms an amide bond or a peptide bond, no racemization occurs; and the operation is simple and the application range is wide.

  本发明公开了一种温和高效的 α-酰氧基烯酰胺化合物的制备方法及其在酰胺和多肽合成中的用途。α-乙酰氧基烯酰胺化合物是通过酰酰胺和羧酸在二氯甲烷中的加成反应得到的，反应条件是温度为0℃至50℃；生成的α-乙酰氧基烯酰胺化合物可以与胺化合物反应生成酰胺或多肽；这两个反应可以逐步进行，也可以在一锅中进行。根据本发明，反应条件温和，不需要金属催化剂；当羧基α位上具有手性的羧酸形成酰胺键或肽键时，不会发生消旋化；操作简单，应用范围广。
• Shippey; Binkley, Journal of Biological Chemistry, 1958, vol. 230, p. 699,700
  作者：Shippey、Binkley

  DOI：——

  日期：——
• PHILPOTT, M. F.;VAN, DER MERWE M. J., CHROMATOGRAPHIA, 31,(1991) N-10, C. 500-504
  作者：PHILPOTT, M. F.、VAN, DER MERWE M. J.

  DOI：——

  日期：——