Cbz-D-Phe-Val-OMe | 15027-26-6

• 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: Cbz-D-Phe-Val-OMe
• 英文别名: (S)-methyl 2-((R)-2-(((benzyloxy)carbonyl)amino)-3-phenylpropanamido)-3-methylbutanoate；2-D-Phenylalanyl-L-valyl-methylester；Z-D-Phe-Val-O-Me；Z-D-Phe-Val-OCH3；methyl (2S)-3-methyl-2-[[(2R)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoyl]amino]butanoate
• CAS: 15027-26-6
• 化学式: C₂₃H₂₈N₂O₅
• 分子量: 412.486
• InChiKey: CEJRBPXRWXOFEP-UXHICEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Cbz-D-Phe-Val-OMe 在 sodium hydroxide 作用下， 生成 N-[(苄氧基)羰基]-D-苯丙氨酰-L-缬氨酸
  参考文献：
  名称：

  Sokotowska,T.; Biernat,J.F., Roczniki Chemii, 1966, vol. 40, p. 1665 - 1673

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄氧羰基-D-苯丙氨酸 、 L-缬氨酸甲酯盐酸盐 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 以91%的产率得到Cbz-D-Phe-Val-OMe
  参考文献：
  名称：

  A novel kinetically-controlled peptide synthesis—Dramatic increase of chemical yield with retention of chiral integrity

  摘要：

  Peptide synthesis employing the highly selective reaction of isobutyl chloroformate at the carboxyl group of the N-protected amino acid, almost to the exclusion of the amino group of the C-protected amino acid, is described. This one-stage, kinetically-controlled strategy remarkably affords peptides with excellent optical purity in high chemical yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01493-8

文献信息

• S-(2-Pyrimidinyl)- and S-(2-(4,6-dimethylpyrimidinyl))-1,1,3,3-tetramethylthiouronium hexafluorophosphates: novel reagents for in situ peptide coupling
  作者：Philip Garner、Özge Şeşenoğlu、H. Ümit Kaniskan

  DOI：10.1016/j.tetlet.2005.11.067

  日期：2006.1

  Two new reagents for in situ peptide coupling based on the 2-mercaptopyrimidine core have been developed. The readily prepared thiouronium salts were found to promote both peptide and segment coupling efficiently with low racemization/epimerization levels.

  已经开发了两种基于2-巯基嘧啶核的用于原位肽偶联的新试剂。发现容易制备的硫脲鎓盐以低消旋化/表观异构化水平有效地促进肽和链段偶联。
• Etude de la racemisation induite par la dmap dans les reactions de couplage peptidique
  作者：Jean-Paul Gamet、Robert Jacquier、Jean verducci

  DOI：10.1016/s0040-4020(01)88439-8

  日期：1984.1

  with H-hydroxybenzotriazole (HOBt). The activation of N-acylated aminoacids by the means of DMAP leads to a complete racemization. On the other hand, for the aminoacids protected under their urethans derivatives, DMAP gives better yields than HOBt with racemization extent generally equal to or slightly higer to that observed with HOBt.

  研究了在肽合成中使用4-二甲基氨基吡啶（DMAP）作为碳二亚胺添加剂的范围和局限性，并与H-羟基苯并三唑（HOBt）获得的结果进行了比较。通过DMAP活化N-酰化的氨基酸导致完全消旋。另一方面，对于在其氨基甲酸酯衍生物保护下的氨基酸，DMAP的收率比HOBt好，外消旋程度通常等于或略高于HOBt。
• An Efficient Light‐Mediated Protocol for the Direct Amide Bond Formation via a Novel Carboxylic Acid Photoactivation Mode by Pyridine‐CBr₄
  作者：Olga G. Mountanea、Danai Psathopoulou、Christiana Mantzourani、Maroula G. Kokotou、E. Alexandros Routsi、Demeter Tzeli、Christoforos G. Kokotos、George Kokotos

  DOI：10.1002/chem.202300556

  日期：2023.6.22

  A UVA-light-mediated synthesis of amides from carboxylic acids and amines or amino acids is presented, taking advantage of a novel photoactivation mode using pyridine-CBr4. Mechanistic studies by DI-HRMS provide experimental evidence for the formation of various intermediates. Application in the synthesis of industrially interesting or bioactive compounds was demonstrated.

  提出了利用吡啶-CBr 4的新型光活化模式，由羧酸和胺或氨基酸UVA光介导合成酰胺。DI-HRMS 的机理研究为各种中间体的形成提供了实验证据。展示了在工业上有趣的或生物活性化合物的合成中的应用。
• Synthesis of Amides and Peptides by Employing [4-(Acetylamino) phenyl]imidodisulfuryl Difluoride (AISF) as a Coupling Reagent
  作者：Swetha Bharamawadeyar、Eti Chetankumar、Chinthaginjala Srinivasulu、Vommina V. Sureshbabu

  DOI：10.1055/s-0043-1763675

  日期：2024.5

  A new synthetic approach for the preparation of amides and peptides containing amino acids as well as aryl acids and amines by employing [4-(acetylamino)phenyl]imidodisulfuryl difluoride (AISF) as a carboxylic acid activator under mild conditions is delineated. The use of AISF as an acid activator allows the reaction to be performed efficiently. This operationally simple amidation is amenable to a
• A novel kinetically-controlled peptide synthesis—Dramatic increase of chemical yield with retention of chiral integrity
  作者：Wen-Chung Shieh、John A. Carlson、Michael E. Shore

  DOI：10.1016/s0040-4039(99)01493-8

  日期：1999.10

  Peptide synthesis employing the highly selective reaction of isobutyl chloroformate at the carboxyl group of the N-protected amino acid, almost to the exclusion of the amino group of the C-protected amino acid, is described. This one-stage, kinetically-controlled strategy remarkably affords peptides with excellent optical purity in high chemical yields. (C) 1999 Elsevier Science Ltd. All rights reserved.