FMOC-苯丙氨酰-L-脯氨酸 | 138372-76-6

• 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
• 中文名称: FMOC-苯丙氨酰-L-脯氨酸
• 英文名称: Fmoc-Phe-Pro-OH
• 英文别名: Fmoc-L-Phe-L-Pro-OH；N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-phenylalaninyl-L-proline；(2S)-1-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]pyrrolidine-2-carboxylic acid
• CAS: 138372-76-6
• 化学式: C₂₉H₂₈N₂O₅
• 分子量: 484.552
• InChiKey: ZLLJYCCFIFHMLH-UIOOFZCWSA-N

物化性质

• 沸点：
  757.8±60.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  FMOC-苯丙氨酰-L-脯氨酸 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 苯并氨酰脯氨酸
  参考文献：
  名称：

  Functional Identification and Structure Determination of Two Novel Prolidases from cog1228 in the Amidohydrolase Superfamily,

  摘要：

  Two uncharacterized enzymes from the amidohydrolase superfamily belonging to cog1228 were cloned, expressed, and purified to homogeneity. The two proteins, Sgx9260c (gi|44242006) and Sgx9260b (gi|44479596), were derived from environmental DNA samples originating from the Sargasso Sea. The catalytic function and substrate profiles for Sgx9260c and Sgx9260b were determined using a comprehensive library of dipeptides and N-acyl derivative of L-amino acids. Sgx9260c catalyzes the hydrolysis of Gly-L-Pro, L-Ala-L-Pro, and N-acyl derivatives of L-Pro. The best substrate identified to date is N-acetyl-L-Pro with a value of k(cat)/K-m of 3 x 10(5) M-1 s(-1). Sgx9260b catalyzes the hydrolysis of L-hydrophobic L-Pro dipeptides and N-acyl derivatives of L-Pro. The best substrate identified to date is N-propionyl-L-Pro with a value of k(cat)/K-m of 1 x 10(5) M-1 s(-1). Three-dimensional structures of both proteins were determined by X-ray diffraction methods (PDB codes 3MKV and 3FEQ). These proteins fold as distorted (beta/alpha)(8)-barrels with two divalent cations in the active site. The structure of Sgx9260c was also determined as a complex with the N-methylphosphonate derivative of L-Pro (PDB code 3N2C). In this structure the phosphonate moiety bridges the binuclear metal center, and one oxygen atom interacts with His-140. The a-carboxylate of the inhibitor interacts with Tyr-231. The proline side chain occupies a small substrate binding cavity formed by residues contributed from the loop that follows beta-strand 7 within the (beta/alpha)(8)-barrel. A total of 38 other proteins from cog1228 are predicted to have the same substrate profile based on conservation of the substrate binding residues. The structure of an evolutionarily related protein, Cc2672 from Caulobacter crecentus, was determined as a complex with the N-methylphosphonate derivative of L-arginine (PDB code 3MTW).

  DOI：

  10.1021/bi100897u
• 作为产物：
  描述：

  Fmoc-L-苯丙氨酸 在 N-甲基吗啉 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.2h， 生成 FMOC-苯丙氨酰-L-脯氨酸
  参考文献：
  名称：

  布朗斯台德酸对微流反应器中混合酸酐/混合碳酸酐活化和无 C 端 N-甲基化肽合成的影响

  摘要：

  使用混合碳酸酐的酰胺化与在叔胺和布朗斯台德酸存在下的混合酸酐之间的比较揭示了酸酐的显着差异。已经开发出通过酰基咪唑鎓快速微流无C端N-甲基化肽合成，且没有严重的外消旋作用。出乎意料地，观察到无C端的N-甲基化二肽的差向异构化。

  DOI：

  10.1002/chem.202401402

文献信息

• Stereoselective Total Synthesis of Marine Cyclodepsipeptide Calcaripeptides A–C
  作者：Sayantan Das、Rajib Kumar Goswami

  DOI：10.1021/jo5019798

  日期：2014.10.17

  The first stereoselective total syntheses of marine cyclodepsipeptides, calcaripeptides A–C, have been accomplished. Emphasis was given particularly in identification of an efficient strategy for the macrocyclization. The notable features of our synthesis include Evans alkylation, Crimmins syn-aldol, Crimmins acetate aldol, Wittig olefination, and Shiina macrolactonization reactions. An anomaly in

  海洋环二肽首个立体选择性全合成钙肽A–C已完成。在确定大环化的有效策略时特别强调。我们合成的显着特征包括埃文斯烷基化，Crimmins顺式醇醛，Crimmins醋酸酯醇醛，Wittig烯烃化反应和Shiina大内酯化反应。在该合成研究过程中，对拟议的钙肽B的1 H NMR异常进行了修正。
• Sureshbabu, Vommina V.; Venkataramanarao, Rao, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 6, p. 910 - 919
  作者：Sureshbabu, Vommina V.、Venkataramanarao, Rao

  DOI：——

  日期：——
• Factors Affecting Conformation in Proline-Containing Peptides
  作者：Carol M. Taylor、Renaud Hardré、Patrick J. B. Edwards、Jae H. Park

  DOI：10.1021/ol035711r

  日期：2003.11.1

  NMR was used to study the thermodynamics of the cis --> trans isomerization for prolyl amide bonds in the compounds shown. The magnitude of K-t/c, for C-terminal esters is greater than for the corresponding amides, signifying stronger backbone stereoelectronic effects in esters. Increasing the steric bulk of the N-terminal residue from Ac- to Ac-Gly- favors the trans conformation. Incorporation of a Phe residue N-terminal to Pro, however, shifts the equilibrium in favor of the cis conformation, via a stabilizing aromatic-proline interaction.
• [EN] METHOD FOR PRODUCING PEPTIDE COMPOUND CONTAINING N-SUBSTITUTED-AMINO ACID RESIDUE<br/>[FR] PROCÉDÉ DE PRODUCTION D'UN COMPOSÉ PEPTIDIQUE CONTENANT UN RÉSIDU D'ACIDE AMINÉ N-SUBSTITUÉ<br/>[JA] Ｎ－置換－アミノ酸残基を含むペプチド化合物の製造方法
  申请人：[en]CHUGAI SEIYAKU KABUSHIKI KAISHA;[ja]中外製薬株式会社

  公开号：WO2022138891A1

  公开（公告）日：2022-06-30

  本発明は、効率的に高純度のペプチド化合物を高収率で製造する方法を提供することを課題とする。固相法における最初の伸長反応に先立って、ペプチドを固相合成用樹脂に担持させることにより、斯かる課題を解決できることを見出した。