N-(N-benzoyl-(O-benzyl-L-threonyl)-L-alanyl-L-phenylalanyl)-L-homoserine lactone

• 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: N-(N-benzoyl-(O-benzyl-L-threonyl)-L-alanyl-L-phenylalanyl)-L-homoserine lactone
• 英文别名: Bz-Thr(Bn)(Bn)-Ala-Phe-Hsl；N-[(2S,3R)-1-oxo-1-[[(2S)-1-oxo-1-[[(2S)-1-oxo-1-[[(3S)-2-oxooxolan-3-yl]amino]-3-phenylpropan-2-yl]amino]propan-2-yl]amino]-3-phenylmethoxybutan-2-yl]benzamide
• 化学式: C₃₄H₃₈N₄O₇
• 分子量: 614.698
• InChiKey: DATCGYVNVMCAKB-AJRHGHNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  152
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-acetoxymethyl-N-(N-benzoyl-(O-benzyl-L-threonyl)-L-alanyl-L-phenylalanyl)-4-oxo-L-homoalanine methyl ester 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 20.0h， 以72%的产率得到N-(N-benzoyl-(O-benzyl-L-threonyl)-L-alanyl-L-phenylalanyl)-L-homoserine lactone
  参考文献：
  名称：

  EP2957555

  摘要：

  公开号：

文献信息

• METHOD FOR MODIFYING DERIVATIVES OF AMINO ACIDS AND PEPTIDES, COMPOUNDS PRODUCED, AND USE
  申请人：Consejo Superior De Investigaciones Científicas (CSIC)

  公开号：EP2957555A1

  公开（公告）日：2015-12-23

  The invention relates to a novel method for modifying hydroxylated cyclic amino acids, especially 4-hydroxyproline, which is a commercial, relatively cheap, natural amino acid, in order to provide other amino acids of high optical purity. The initial step of the process is a free-radical excision, and the excision product converts itself into non-proteinogenic amino acids by means of reactions such as reduction, reductive amination, and Horner-Wadsworth-Emmons reactions. The method is characterised in that it is applicable to the selective modification of peptides. The invention also relates to the products of said method, such as amino acids that are N-alkylated and/or have side chains with groups of amino, hydroxyl, alkenyl etc., and to the peptidic derivatives thereof of interest as pharmaceuticals, catalysts, molecular imaging probes etc.

  本发明涉及一种新方法，用于修饰羟基环状氨基酸，特别是 4-羟基脯氨酸，这是一种商品化的、相对廉价的天然氨基酸，以提供其他高光学纯度的氨基酸。该工艺的第一步是自由基切除，切除产物通过还原、还原胺化和 Horner-Wadsworth-Emmons 反应等反应转化为非蛋白源氨基酸。该方法的特点是适用于肽的选择性修饰。本发明还涉及上述方法的产物，如经过 N-烷基化和/或具有氨基、羟基、烯基等基团侧链的氨基酸，以及作为药物、催化剂、分子成像探针等的肽衍生物。
• Creating Diversity by Site-Selective Peptide Modification: A Customizable Unit Affords Amino Acids with High Optical Purity
  作者：Ivan Romero-Estudillo、Alicia Boto

  DOI：10.1021/ol402800a

  日期：2013.11.15

  The development of peptide libraries by site-selective modification of a few parent peptides would save valuable time and materials in discovery processes, but still is a difficult synthetic challenge. Herein natural hydroxyproline is introduced as a "convertible" unit for the production of a variety of optically pure amino acids, including expensive N-alkyl amino acids, and to achieve the mild, efficient, and site-selective modification of peptides.
• [EN] METHOD FOR MODIFYING DERIVATIVES OF AMINO ACIDS AND PEPTIDES, COMPOUNDS PRODUCED, AND USE<br/>[ES] PROCEDIMIENTO DE MODIFICACIÓN DE DERIVADOS DE AMINOÁCIDOS Y PÉPTIDOS, COMPUESTOS OBTENIDOS Y UTILIZACIÓN<br/>[FR] PROCÉDÉ DE MODIFICATION DE DÉRIVÉS D'ACIDES AMINÉS ET DE PEPTIDES, COMPOSÉS OBTENUS ET UTILISATION CORRESPONDANTE
  申请人：CONSEJO SUPERIOR INVESTIGACION

  公开号：WO2014125145A1

  公开（公告）日：2014-08-21

  La presente invención describe un nuevo procedimiento para la modificación de amino ácidos cíclicos hidroxilados, particularmente la 4-hidroxiprolina, que es un amino ácido natural, comercial y relativamente barato, para dar otros amino ácidos de alta pureza óptica. El paso inicial del proceso es una escisión radicalaria, y el producto de escisión se convierte en amino ácidos no proteinogénicos usando reacciones como por ejemplo la reducción, la aminación reductiva, y la Horner-Wadsworth-Emmons. Es de destacar la aplicación del procedimiento a la modificación selectiva de péptidos. También se describen los productos de dicho procedimiento, como amino ácidos N-alquilados y/o con cadenas laterales con grupos amino, hidroxilo, alquenilo, etc. y sus derivados peptídicos, de interés como fármacos, catalizadores, sondas para imagen molecular, etc.