Z-Glu(O-t-Bu)-Ala-OMe | 5249-68-3

• 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: Z-Glu(O-t-Bu)-Ala-OMe
• 英文别名: Cbz-Glu(OtBu)-Ala-OMe；tert-butyl (4S)-5-[[(2S)-1-methoxy-1-oxopropan-2-yl]amino]-5-oxo-4-(phenylmethoxycarbonylamino)pentanoate
• CAS: 5249-68-3
• 化学式: C₂₁H₃₀N₂O₇
• 分子量: 422.478
• InChiKey: WSPZAHXJKVTWPB-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Z-Glu(O-t-Bu)-Ala-OMe 在 钯 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 9.0h， 生成 N-benzyloxycarbonyl-L-valyl-γ-tert-butyl-L-glutamyl-L-alanine methyl ester
  参考文献：
  名称：

  Kolomeitseva, L. A.; Kocharova, N. A.; Ibragimova, L. D., Journal of general chemistry of the USSR, 1982, vol. 52, # 2, p. 372 - 377

  摘要：

  DOI：
• 作为产物：
  描述：

  N-[苄氧羰基]-L-谷氨酸 5-叔丁酯 1-甲酯 在 2-羟基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Z-Glu(O-t-Bu)-Ala-OMe
  参考文献：
  名称：

  Polypeptides with Known Repeating Sequence of Amino Acids. Synthesis of Poly-L-glutamyl-L-alanyl-L-glutamic Acid and Polyglycylglycyl-L-phenylalanine through Pentachlorophenyl Active Ester¹

  摘要：

  DOI：

  10.1021/ja00962a035

文献信息

• Synthesis of Peptides Employing Protected-Amino Acid Halides Mediated by Commercial Anion Exchange Resin
  作者：K. M. Bhaskara Redddy、Y. Bharathi Kumari、Kuppanna Ananda

  DOI：10.1007/s10989-012-9337-5

  日期：2013.9

  AbstractCoupling of protected-amino acid halides (chloride, fluoride) mediated by commercial anion exchange resin for the solution phase synthesis of peptides is described. The reaction was carried out in an organic medium, circumventing the use of an organic base or an inorganic base. The coupling is fast, clean and racemization free. The anion exchange resin functions as a solid-phase basic scavenger

  摘要描述了由商业阴离子交换树脂介导的用于肽的溶液相合成的受保护氨基酸卤化物（氯化物，氟化物）的偶联。该反应在有机介质中进行，从而避免了使用有机碱或无机碱。联轴器快速，清洁且无外消旋。阴离子交换树脂起着固相碱性清除剂的作用，吸收产生的HCl，并使胺发生反应。该方法被扩展用于空间位阻的α，α，-二烷基氨基酸的偶联。 图形概要
• tert-Butyloxycarbonyl and benzyloxycarbonyl amino acid fluorides. New, stable rapid-acting acylating agents for peptide synthesis
  作者：Louis A. Carpino、El-Sayed M. E. Mansour、Dean Sadat-Aalaee

  DOI：10.1021/jo00008a005

  日期：1991.4

  A new class of rapid-acting acylating agents, alpha-BOC and Z amino acid fluorides are obtained as stable, often crystalline, compounds by treatment of the protected amino acid with cyanuric fluoride.
• Macrocyclization of Peptide Side Chains by the Ugi Reaction: Achieving Peptide Folding and Exocyclic <i>N</i>-Functionalization in One Shot
  作者：Aldrin V. Vasco、Carlos S. Pérez、Fidel E. Morales、Hilda E. Garay、Dimitar Vasilev、José A. Gavín、Ludger A. Wessjohann、Daniel G. Rivera

  DOI：10.1021/acs.joc.5b00858

  日期：2015.7.2

  The cyclization of peptide side chains has been traditionally used to either induce or stabilize secondary structures (beta-strands, helices, reverse turns) in short peptide sequences. So far, classic peptide coupling, nucleophilic substitution, olefin metathesis, and click reactions have been the methods of choice to fold synthetic peptides by means of macrocyclization. This article describes the utilization of the Ugi reaction for the side chain-to-side chain and side chain-to-termini macrocydization of peptides, thus enabling not only access to stable folded structures but also the incorporation of exocydic functionalities as N-substituents. Analysis of the NMR-derived structures revealed the formation of helical turns, beta-bulges, and a-turns in cyclic peptides cross-linked at i, i + 3 and i, i + 4 positions, proving the folding effect of the multicomponent Ugi macrocyclization. Molecular dynamics simulation provided further insights on the stability and molecular motion of the side chain cross-linked peptides.
• Chakravarty,P.K. et al., Indian Journal of Chemistry, 1974, vol. 12, p. 464 - 470
  作者：Chakravarty,P.K. et al.

  DOI：——

  日期：——
• Synthesis of Polypeptides with Known Repeating Sequence of Amino Acids
  作者：J. Kovacs、A. Kapoor

  DOI：10.1021/ja01079a021

  日期：1965.1