Fmoc-Leu-Pro-OH | 130832-25-6

• 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: Fmoc-Leu-Pro-OH
• 英文别名: (2S)-1-[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-methylpentanoyl]pyrrolidine-2-carboxylic acid
• CAS: 130832-25-6
• 化学式: C₂₆H₃₀N₂O₅
• 分子量: 450.535
• InChiKey: FITYSLDOLQCIDF-GOTSBHOMSA-N

物化性质

• 沸点：
  684.9±55.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 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-Leu-Pro-OH 在 哌啶 、 1,4-丁二硫醇 、 mesna 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 达卡巴嗪 、 4-羟乙基哌嗪乙磺酸 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 methyl (2R)-2-[[(2S)-1-[(2S)-4-methyl-2-[[2-[[(2S)-4-methylsulfanyl-2-[[(2R)-2-[[2-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]acetyl]amino]-3-sulfanylpropanoyl]amino]butanoyl]amino]acetyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylpropanoate
  参考文献：
  名称：

  Efficient Synthesis of a Fluorescent Farnesylated Ras Peptide

  摘要：

  DOI：

  10.1021/jo015526w
• 作为产物：
  描述：

  (S)-methyl 1-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-methylpentanoyl)pyrrolidine-2-carboxylate 在 lithium hydroxide monohydrate 、 calcium chloride 作用下， 以 四氢呋喃 、 水 、 异丙醇 为溶剂， 反应 0.75h， 以95%的产率得到Fmoc-Leu-Pro-OH
  参考文献：
  名称：

  含脯氨酸环肽及其线性类似物和同源物的合成及抗癌活性

  摘要：

  摘要 采用液相法合成含脯氨酸的环状五肽 2 和天然存在的环状七肽 Reniochalistatin B 3 的全合成。对于 3 的合成，采用发散和收敛策略，将总产率从 12 提高到25%。合成了不同的 N 和 C 末端修饰的线性类似物以及 2 和 3 的同源物。环肽 2 和 3 及其线性类似物/同源物均评估了对 HeLa 细胞系的抗癌活性，其中具有 N 末端保护的六氟异丙基氨基甲酸酯 (HFIPC) 的五肽 2 h 和六肽 3n 有趣地显示出更高的细胞毒性，IC50 为2.73 和 4.3 µM，分别与其 Boc 保护的类似物 2a (IC50 20 µM) 和 3c (IC50 38.51 µM) 和环肽 2 (> 100 µM) 和 3 (47 µM)。这些结果通过集落形成和伤口愈合试验等生物学实验得到了进一步验证。图形概要

  DOI：

  10.1080/00397911.2018.1550201

文献信息

• Thermal Cleavage of the Fmoc Protection Group
  作者：Stefan Höck、Roger Marti、Rainer Riedl、Marina Simeunovic

  DOI：10.2533/chimia.2010.200

  日期：——

  The Fmoc protection group is among the most commonly used protection groups for the amino function. A fast method for the thermal deavage of this protection group under base-free conditions without the need for dibenzofulvene scavengers is presented. The advantages of this method include straightforward testability by means of a simple high-temperature NMR experiment, usually high yields, and good selectivity towards the BOC protection group and t-butyl ethers.

  Fmoc保护基是氨基功能中最常用的保护基之一。在无碱条件下快速去除这种保护基的热解方法，无需二苯并富烯清除剂。该方法的优点包括通过简单的高温NMR实验进行直接测试，通常高产率，并且对BOC保护基和叔丁基醚具有良好的选择性。
• Solid-phase synthesis of palmitoylated and farnesylated lipopeptides employing the fluoride-labile PTMSEL linker
  作者：Maria Lumbierres、Jose M. Palomo、Goran Kragol、Herbert Waldmann

  DOI：10.1016/j.tetlet.2006.02.109

  日期：2006.4

  Acid- and base-labile S-palmitoylated and S-farnesylated lipopeptides can be synthesized in high overall yield employing the (2-phenyl-2-trimethylsilyl) ethyl (PTMSEL) linker for anchoring to and release under almost neutral conditions from the solid support.

  可以使用（2-苯基-2-三甲基甲硅烷基）乙基（PTMSEL）接头固定并在几乎中性的条件下从固体载体上以高收率合成酸和碱不稳定的S-棕榈酰化和S-法呢基化的脂肽。
• Piperidine is preferred to morpholine for Fmoc cleavage in solid phase glycopeptide synthesis as exemplified by preparation of glycopeptides related to HIV gp120 and mucins
  作者：Tatjana Vuljanic、Karl-Erik Bergquist、Henrik Clausen、Sarbari Roy、Jan Kihlberg

  DOI：10.1016/0040-4020(96)00369-9

  日期：1996.6

  deallylation. The derivatives 5 and 8 were used for solid phase synthesis of glycopeptides related to HIV gp120 and mucins. In these syntheses piperidine was found to give efficient Fmoc removal whereas deprotection with morpholine was slow and incomplete for some steps. In contrast to previous concerns β-elimination and epimerization of glycopeptide stereocenters was not encountered when piperidine

  在Tn的抗原[将Fmoc-丝氨酸/苏氨酸（AC的被保护的衍生物3 GalNAcα）-OH，化合物5和8 ]已经制备通过将Fmoc-丝氨酸/苏氨酸- O-烯丙基糖基化与3,4,6-三- ø -乙酰基-2-叠氮基-2-脱氧-D-吡喃半乳糖基氯（2），然后将叠氮基转化为乙酰胺并脱脱甲酰。导数5和8用于固相合成与HIV gp120和粘蛋白有关的糖肽。在这些合成中，发现哌啶可有效去除Fmoc，而吗啉的脱保护作用缓慢且在某些步骤中不完全。与先前的关注相反，当哌啶用于Fmoc脱保护时，没有遇到糖肽立体中心的β-消除和差向异构化。然而，发现对于糖肽而言，其侧链脱保护并从固相切割。
• Synthesis of characteristic lipopeptides of the human N-Ras protein and their evaluation as possible inhibitors of protein farnesyl transferase
  作者：Paul Stöber、Michael Schelhaas、Edgar Nägele、Patrizia Hagenbuch、János Rétey、Herbert Waldmann

  DOI：10.1016/s0968-0896(96)00213-1

  日期：1997.1

  N-Ras protein, was prepared. If acid labile blocking functions like the Boc group were used, upon deprotection an undesired addition of the acid to the double bonds of the farnesyl residue occurred. Therefore, acid labile blocking groups should not be employed in the synthesis of farnesylated lipopeptides. The lipopeptide methyl esters which carry only a farnesyl group do not inhibit protein farnesyl

  带有法呢基硫醚或棕榈酸硫酯和法呢基硫醚的脂肽是通过使用钯（0）敏感的Aloc氨基甲酸酯的碱基不稳定的Fmoc封闭基团通过肽链的N端延伸从S-法呢基半胱氨酸甲酯制备的。通过该技术，制备了代表人N-Ras蛋白的完全官能化的，即棕榈酰化的和法尼基化的C末端的脂六肽。如果使用诸如Boc基团之类的对酸不稳定的阻断功能，则在脱保护时，会发生不希望的酸加到法呢基残基的双键上。因此，酸不稳定的保护基团不应用于合成法呢基脂肽。仅带有法呢基的脂肽甲酯不会抑制蛋白法呢基转移酶，
• Functional Identification and Structure Determination of Two Novel Prolidases from cog1228 in the Amidohydrolase Superfamily,
  作者：Dao Feng Xiang、Yury Patskovsky、Chengfu Xu、Alexander A. Fedorov、Elena V. Fedorov、Abby A. Sisco、J. Michael Sauder、Stephen K. Burley、Steven C. Almo、Frank M. Raushel

  DOI：10.1021/bi100897u

  日期：2010.8.10

  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).