N-芴甲氧羰基-丙氨酰-脯氨酸 | 186023-44-9

• 物质功能分类: 生物化工 - 氨基酸及其衍生物
• 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: N-芴甲氧羰基-丙氨酰-脯氨酸
• 英文名称: Fmoc-Ala-Pro-OH
• 英文别名: (2S)-1-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyl]pyrrolidine-2-carboxylic acid
• CAS: 186023-44-9
• 化学式: C₂₃H₂₄N₂O₅
• 分子量: 408.454
• InChiKey: HLFCRSYTJCARCY-XOBRGWDASA-N

物化性质

• 沸点：
  674.0±55.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  N-芴甲氧羰基-丙氨酰-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 L-丙氨酰基-L-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：

  L-脯氨酸苄酯盐酸盐 在 palladium on activated charcoal 氰基磷酸二乙酯 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 N-芴甲氧羰基-丙氨酰-脯氨酸
  参考文献：
  名称：

  海洋代谢物树干酰胺A的全合成和立体化学修订。

  摘要：

  细胞毒Lissoclinum sp。的分离。1996年报道了代谢产物树干酰胺A。在1999年完成全部合成后，很明显必须对该海洋天然产物的结构进行修改。现在，我们报告在完全合成中首次制备实际的树干酰胺A的过程，可以明确地证明其结构和立体化学性质。我们合成策略的重点是路易斯酸辅助的氮丙啶开环，该开环用于制备新型的反向预炔化的丝氨酸和苏氨酸侧链，以及在大环骨架上有效的恶唑啉-噻唑啉互变。此外，通过互补合成方案制备的几种立体异构体可用于说明我们方法的一般范围并确认构型分配。

  DOI：

  10.1021/jo9914566

文献信息

• Aldehyde Capture Ligation for Synthesis of Native Peptide Bonds
  作者：Monika Raj、Huabin Wu、Sarah L. Blosser、Marc A. Vittoria、Paramjit S. Arora

  DOI：10.1021/jacs.5b03538

  日期：2015.6.3

  reactions for amide bond formation have transformed the ability to access synthetic proteins and other bioconjugates through ligation of fragments. In these ligations, amide bond formation is accelerated by transient enforcement of an intramolecular reaction between the carboxyl and the amine termini of two fragments. Building on this principle, we introduce an aldehyde capture ligation that parlays

  酰胺键形成的化学选择性反应改变了通过片段连接获得合成蛋白质和其他生物偶联物的能力。在这些连接中，两个片段的羧基和胺末端之间的分子内反应的瞬时增强加速了酰胺键的形成。基于这一原则，我们引入了一种醛捕获连接，它利用醛和胺的高化学选择性反应性来加强现有技术难以连接的氨基酸残基和肽之间的酰胺键形成。
• ALDEHYDE CAPTURE LIGATION TECHNOLOGY FOR SYNTHESIS OF AMIDE BONDS
  申请人：New York University

  公开号：US20170247324A1

  公开（公告）日：2017-08-31

  The present invention relates to ligation agents and their use in making an amide ligation product. Methods of making the ligation agents are also disclosed.

  本发明涉及连接剂及其在制备酰胺连接产物中的应用。还公开了制备连接剂的方法。
• A catalytic one-step synthesis of peptide thioacids: the synthesis of leuprorelin <i>via</i> iterative peptide–fragment coupling reactions
  作者：Takuya Matsumoto、Koki Sasamoto、Ryo Hirano、Kounosuke Oisaki、Motomu Kanai

  DOI：10.1039/c8cc07935h

  日期：——

  A catalytic one-step synthesis of peptide thioacids was developed. The oxygen–sulfur atom exchange reaction converted the carboxy group at the C-terminus of the peptides into a thiocarboxy group with suppressed epimerization. This method was successfully applied to the synthesis of the peptide drug leuprorelin via an iterative fragment-coupling protocol.

  开发了一种催化一步合成肽硫代酸的方法。氧-硫原子交换反应将肽C-末端的羧基转化为差向异构化的硫代羧基。该方法已通过迭代片段偶联方案成功应用于肽药物亮丙瑞林的合成。
• Convergent Solid-Phase Synthesis of Macromolecular MUC1 Models Truly Mimicking Serum Glycoprotein Biomarkers of Interstitial Lung Diseases
  作者：Naoki Ohyabu、Kiyoshi Kakiya、Yasuhiro Yokoi、Hiroshi Hinou、Shin-Ichiro Nishimura

  DOI：10.1021/jacs.6b04973

  日期：2016.7.13

  macromolecular MUC1 glycopeptides have been used to unravel molecular mechanisms in antibody recognition of disease-specific epitopes. We have established a novel synthetic strategy for MUC1 tandem repeats having complex O-glycosylation states at each repeating unit based on convergent solid-phase fragment condensation under microwave irradiation. We have accomplished the synthesis of 77 amino acid MUC1 glycopeptides

  合成的大分子 MUC1 糖肽已被用于揭示抗体识别疾病特异性表位的分子机制。我们已经建立了一种新的 MUC1 串联重复合成策略，该策略基于微波辐射下的收敛固相片段缩合，在每个重复单元上具有复杂的 O-糖基化状态。我们已经在 19 个潜在 O-糖基化位点中的 10 个指定位置完成了 77 个氨基酸 MUC1 糖肽（MW = 12 759）的合成，该糖肽具有三种主要的抗原性 O-糖型 [Tn、核心 1 (T) 和核心 2 结构] .
• Pseudo-Prolines as a Molecular Hinge:  Reversible Induction of <i>cis</i> Amide Bonds into Peptide Backbones
  作者：Pascal Dumy、Michael Keller、Declan E. Ryan、Barbara Rohwedder、Torsten Wöhr、Manfred Mutter

  DOI：10.1021/ja962780a

  日期：1997.2.1

  Serine, threonine-derived (4S)-oxazolidine-4-carboxylic acid, and cysteine-derived (4R)-thiazolidinecarboxylic acid, denoted pseudo-proline (Xaa[Psi(R1,R2)pro]), serve as structure disrupting, solubilizing building blocks in peptide synthesis. Variation of the 2-C substituents within the heterocyclic system results in different physicochemical and conformational properties. NMR studies of a series of pseudo-proline (Psi Pro)-containing peptides reveal a pronounced effect of the 2-C substituents upon the cis to trans ratio of the adjacent amide bond in solution. 2-C unsubstituted systems show a preference similar to that of the proline residue for the trans form, whereas 2,2-dimethylated derivatives adopt the cis amide conformation in high content. For 2-monosubstituted Psi Pro, the cis-trans distribution depends on the 2-C chirality. For the 2-(S)-diastereoisomer, both forms are similarly populated in solution, whereas the 2-(R)-epimer adopts preferentially the trans form. The results are supported by conformational energy calculations and suggest that, by tailoring the degree of substitution, pseudo-prolines may serve as a temporary proline mimetic or as a hinge in peptide backbones.