cyclo[Leu-3-MeAzy-Phe-Gly] | 1351234-64-4

• 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: cyclo[Leu-3-MeAzy-Phe-Gly]
• 英文别名: cyclo[Leu-(3-methylaziridine-2-carboxylic acid)-Phe-Gly]；(3S,9S,12S,13S)-9-benzyl-3-isobutyl-13-methyl-1,4,7,10-tetraazabicyclo[10.1.0]tridecane-2,5,8,11-tetraone；cyclo[Azi(Me)(Me)-Phe-Gly-Leu]；(3S,9S,12S,13S)-9-benzyl-13-methyl-3-(2-methylpropyl)-1,4,7,10-tetrazabicyclo[10.1.0]tridecane-2,5,8,11-tetrone
• CAS: 1351234-64-4
• 化学式: C₂₁H₂₈N₄O₄
• 分子量: 400.478
• InChiKey: WUJUXHGRIZOIAE-FFSBBHALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cyclo[Leu-3-MeAzy-Phe-Gly] 在 N,N-二异丙基乙胺 、 (1,2,3-benzotriazol-1-yloxy)tris(dimethylamino)phosphanium hexafluoro-lambda5-phosphanuide 、 lithium hydroxide 作用下， 以 水 、 二甲基亚砜 、 乙腈 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Site-Specific Integration of Amino Acid Fragments into Cyclic Peptides

  摘要：

  The concept of site-specific integration of fragments into macrocyclic entities has not yet found application in the realm of synthetic chemistry. Here we show that the reduced amidicity of aziridine amide bonds provides an entry point for the site-specific integration of amino acids and peptide fragments into the homodetic cyclic peptide architecture. This new synthetic operation improves both the convergence and divergence of cyclic peptide synthesis.

  DOI：

  10.1021/ja412256f
• 作为产物：
  描述：

  N-烯丙氧羰基-L-亮氨酸 在 四(三苯基膦)钯 、 巴比妥酸 、 N-羟基-7-氮杂苯并三氮唑 、 PyBOP 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 、 氯仿 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 cyclo[Leu-3-MeAzy-Phe-Gly]
  参考文献：
  名称：

  A Versatile Scaffold for Site-Specific Modification of Cyclic Tetrapeptides

  摘要：

  A novel scaffold that can be used to prepare conformationally homogeneous cyclic tetrapeptides equipped with a beta-amino acid residue is disclosed. It Is shown that regioselective structural modification can be accomplished using thiols and azide nucleophiles, commonly associated with rich downstream chemistry. The method should find application in efforts to constrain privileged tripeptide sequences in rigid molecular scaffolds.

  DOI：

  10.1021/ol301178r

文献信息

• [EN] CYCLIC AMINO ACID MOLECULES CONTAINING AZIRIDINE AMINO ACIDS AND METHODS OF PREPARING SAME<br/>[FR] MOLÉCULES D'ACIDES AMINÉS CYCLIQUES CONTENANT DES ACIDES AMINÉS D'AZIRIDINE ET LEURS PROCÉDÉS DE PRÉPARATION
  申请人：UNIV TORONTO

  公开号：WO2011150500A1

  公开（公告）日：2011-12-08

  Cyclic amino acid molecules containing aziridine amino acids are provided, as well as methods of preparing same. Linear peptides containing aziridine amino acids and methods of preparing same are also provided.
• A Versatile Scaffold for Site-Specific Modification of Cyclic Tetrapeptides
  作者：Christopher J. White、Andrei K. Yudin

  DOI：10.1021/ol301178r

  日期：2012.6.1

  A novel scaffold that can be used to prepare conformationally homogeneous cyclic tetrapeptides equipped with a beta-amino acid residue is disclosed. It Is shown that regioselective structural modification can be accomplished using thiols and azide nucleophiles, commonly associated with rich downstream chemistry. The method should find application in efforts to constrain privileged tripeptide sequences in rigid molecular scaffolds.
• Site-Specific Integration of Amino Acid Fragments into Cyclic Peptides
  作者：Christopher J. White、Jennifer L. Hickey、Conor C. G. Scully、Andrei K. Yudin

  DOI：10.1021/ja412256f

  日期：2014.3.12

  The concept of site-specific integration of fragments into macrocyclic entities has not yet found application in the realm of synthetic chemistry. Here we show that the reduced amidicity of aziridine amide bonds provides an entry point for the site-specific integration of amino acids and peptide fragments into the homodetic cyclic peptide architecture. This new synthetic operation improves both the convergence and divergence of cyclic peptide synthesis.