benzyl (S)-4-((tert-butoxycarbonyl)amino)-5-oxo-5-(phenylamino)pentanoate | 126349-57-3

• 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: benzyl (S)-4-((tert-butoxycarbonyl)amino)-5-oxo-5-(phenylamino)pentanoate
• 英文别名: N-phenyl-N-α-tert-butoxycarbonyl-γ-benzyl ester L-glutamide；benzyl 4-(tert-butoxycarbonyl-amino)-5-oxo-5-(phenylamino)pentanoate；benzyl 4(S)-(tert-butoxycarbonylamino)-5-oxo-5-(phenylamino)pentanoate；benzyl (4S)-5-anilino-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoate
• CAS: 126349-57-3
• 化学式: C₂₃H₂₈N₂O₅
• 分子量: 412.486
• InChiKey: FLIAZKXOQIOEIW-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：

  benzyl (S)-4-((tert-butoxycarbonyl)amino)-5-oxo-5-(phenylamino)pentanoate 在 N-甲基吗啉 、 盐酸 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.83h， 生成
  参考文献：
  名称：

  Phosphotyrosine-Containing Dipeptides as High-Affinity Ligands for the p56^lck SH2 Domain

  摘要：

  Src homology-2 (SH2) domains are noncatalytic motifs containing approximately 100 amino acid residues that are involved in intracellular signal transduction. The phosphotyrosine-containing tetrapeptide Ac-pYEEI binds to the SH2 domain of p.56(lck) (Lck) with an affinity of 0.1 mu M. Starting from Ac-pYEEI, we have designed potent antagonists of the Lck SH2 domain which are reduced in peptidic character and in which the three carboxyl groups have been eliminated. The two C-terminal amino acids (EI) have been replaced by benzylamine derivatives and the pY + 1 glutamic acid has been substituted with leucine. The best C-terminal fragment identified, (S)-1-(4-isopropylphenyl)ethylamine, binds to the Lck SH2 domain better than the C-terminal dipeptide EI. Molecular modeling suggests that the substituents at the 4-position of the phenyl ring occupy the pY + 3 lipophilic pocket in the SH2 domain originally occupied by the isoleucine side chain. This new series of phosphotyrosine-containing dipeptides binds to the Lck SH2 domain with potencies comparable to that of tetrapeptide 1.

  DOI：

  10.1021/jm980612i
• 作为产物：
  描述：

  N-叔丁氧羰基-L-谷氨酸 5-苄酯 在 哌啶 、 4-二甲氨基吡啶 、 N,O-双三甲硅基乙酰胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 benzyl (S)-4-((tert-butoxycarbonyl)amino)-5-oxo-5-(phenylamino)pentanoate
  参考文献：
  名称：

  In Situ Carboxyl Activation Using a Silatropic Switch: A New Approach to Amide and Peptide Constructions

  摘要：

  The novel reactivity of O-silylthionoesters with amine nucleophiles to generate oxoamides (rather than thioamides) is described. A straightforward first-generation trimethylsilylation protocol using bistrimethylsilylacetamide (BSA) combined with the unique reactivity of the O-silylthionoesters toward 1 degrees and 2 degrees amines to generate oxoamides provides the simplest means of activating a thiol acid for peptide bond formation at neutral pH. Excellent stereoretention is observed.

  DOI：

  10.1021/ja2065158

文献信息

• Processes for forming amide bonds and compositions related thereto
  申请人：Liebeskind Lanny S.

  公开号：US08921599B2

  公开（公告）日：2014-12-30

  The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.

  该公开涉及生产酰胺键的方法及相关试剂。在某些实施例中，该公开涉及通过混合O-硅烷基硫酸酯和胺在条件下生产酰胺的方法。在另一实施例中，该公开涉及混合硫酸酯、硅基化剂和胺在条件下形成酰胺。
• 1-(SULFONYL)-N-PHENYLPYRROLIDINE-2-CARBOXAMIDES FOR THE IDENTIFICATION OF BIOLOGICAL AND PHARMACOLOGICAL ACTIVITY
  申请人：Castells Boliart Josep

  公开号：US20120142936A1

  公开（公告）日：2012-06-07

  Novel compounds are continually sought after to treat and prevent diseases and disorders. The invention relates to 1-(sulfonyl)-N-phenylpyrrolidine-2-carboxamides which are useful for being biologically and pharmacologically screened, and to contribute to the exploration and identification of new lead molecules that are capable of modulating the functional activity of a biological target.

  小说化合物不断被寻求用于治疗和预防疾病和紊乱。该发明涉及对1-(磺酰基)-N-苯基吡咯烷-2-羧酰胺的利用，这些化合物有助于进行生物学和药理学筛选，并有助于探索和鉴定能够调节生物靶标功能活性的新引物分子。
• Controlled ring-opening polymerization of α-amino acid N-carboxy-anhydride by frustrated amine/borane Lewis pairs
  作者：Hongyuan Zhang、Yanzhao Nie、Xinmei Zhi、Haifeng Du、Jing Yang

  DOI：10.1039/c7cc01440f

  日期：——

  In this paper, we presented a novel strategy to control ROP of -amino acid N-carboxy-anhydrides using the concept of frustrated Lewis pairs (FLPs). An FLP intermediate containing an interaction between the bulky borane Lewis acid and the amine groups of the propagation chain end is essential to accomplish the polypeptide synthesis with well-defined structures under mild conditions.

  在本文中，我们提出了一种使用沮丧的路易斯对（FLP）概念控制β-氨基酸N-羧基酐的ROP的新策略。含有庞大的硼烷路易斯酸和传播链末端的胺基之间相互作用的FLP中间体对于在温和条件下完成具有明确结构的多肽合成至关重要。
• EP2452934
  申请人：——

  公开号：——

  公开（公告）日：——
• New orally active enkephalinase inhibitors: their synthesis, biological activity, and analgesic properties
  作者：Kazuhiko Senokuchi、Hisao Nakai、Yuuki Nagao、Yasuhiro Sakai、Nobuo Katsube、Masanori Kawamura

  DOI：10.1016/s0968-0896(97)10048-7

  日期：1998.4

  A series of (4S)-4-[(2S)-benzyl-3-mercaptopropionylamino]-4-(N-phenylcarbamoyl)-butyric acids has been identified as potent systemically active enkephalinase inhibitors. Structure-activity relationships (SAR) are discussed. Further chemical modification of the inhibitors was carried out in order to identify the inhibitors which are orally active in an animal model. Compounds of particular interest are the prodrug-like analogues, including 5b (ONO-9902). Their analgesic effects after oral administration were evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.