N-[(9H-芴-9-基甲氧基)羰基]甘氨酰-L-脯氨酸 | 212651-48-4

• 物质功能分类: 生物 - 细胞培养 - 添加剂
• 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-[(9H-芴-9-基甲氧基)羰基]甘氨酰-L-脯氨酸
• 英文名称: N-(9H-fluoren-9-ylmethoxycarbonyl)glycyl-L-proline
• 英文别名: Fmoc-Gly-Pro-OH；Fmoc-Gly-Pro；(2S)-1-[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]pyrrolidine-2-carboxylic acid
• CAS: 212651-48-4
• 化学式: C₂₂H₂₂N₂O₅
• 分子量: 394.427
• InChiKey: HPTFPWMPQFBSHP-IBGZPJMESA-N

物化性质

• 沸点：
  676.5±55.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 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-[(9H-芴-9-基甲氧基)羰基]甘氨酰-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 甘油-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：

  Methyl phosphonated L-Arginine 在 cocktail R 作用下， 反应 3.0h， 生成 N-[(9H-芴-9-基甲氧基)羰基]甘氨酰-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

文献信息

• A convenient preparation of several N-linked glycoamino acid building blocks for efficient solid-phase synthesis of glycopeptides
  作者：Jeroen van Ameijde、H. Bauke Albada、Rob M. J. Liskamp

  DOI：10.1039/b201296k

  日期：2002.4.9

  A convenient, high yielding route for the preparation of several Boc- and Fmoc-protected N-linked glycopeptide monomers is presented. These building blocks can be used for the solid-phase synthesis of glycopeptides or glycopeptidomimetics, which is exemplified by the preparation of an N-linked dodecaglycopeptide Ac–(GlyProAsn[Gal])4–NH2, a potential collagen mimic.

  本研究提出了一条便捷且产率高的制备多个Boc和Fmoc保护的N-连接糖肽单体的方法。这些构建单元可用于糖肽或糖肽模拟物的固相合成，通过制备N-连接的十二糖肽Ac–(GlyProAsn[Gal])4–NH2为例，展示了其作为潜在胶原蛋白模拟物的应用。
• Peptide Bond Isosteres:  Ester or (<i>E</i>)-Alkene in the Backbone of the Collagen Triple Helix
  作者：Cara L. Jenkins、Melissa M. Vasbinder、Scott J. Miller、Ronald T. Raines

  DOI：10.1021/ol050780m

  日期：2005.6.1

  [structure: see text] Collagen is the most abundant protein in animals. Interstrand N-H...O=C hydrogen bonds between backbone amide groups form a ladder in the middle of the collagen triple helix. Isosteric replacement of the hydrogen-bond-donating amide with an ester or (E)-alkene markedly decreases the conformational stability of the triple helix. Thus, this recurring hydrogen bond is critical to the

  [结构：参见文字]胶原蛋白是动物中最丰富的蛋白质。主链酰胺基团之间的链间NH ... O = C氢键在胶原三螺旋的中间形成一个阶梯。用酯或（E）-烯烃的等氢取代给氢键的酰胺显着降低了三螺旋的构象稳定性。因此，这种重复的氢键对于胶原蛋白的结构完整性至关重要。在这种情况下，与（E）-链烯相比，酯-等排烷酯具有更高的稳定性。
• Design and synthesis of peptide-based macrocyclic cyclophilin inhibitors
  作者：Brett A. Granger、Dean G. Brown

  DOI：10.1016/j.bmcl.2016.09.039

  日期：2016.11

  The efficient assembly of an 18-membered macrocyclic peptide core was realized by a straightforward and convergent approach utilizing ring-closing metathesis of the corresponding linear tetrapeptides as the key transformation. This approach allowed for the facile preparation of a focused library of novel macrocycles that culminated in the discovery of a cyclophilin A inhibitor with a Kd = 5.4 μM.

  18元大环肽核心的有效组装是通过一种简单且收敛的方法实现的，该方法利用相应线性四肽的闭环复分解作为关键转化。这种方法使该最终在一个亲环素A抑制剂的发现具有新颖大环化合物的聚焦文库的容易制备ķ d  = 5.4微米。
• Rotaxanes of Cyclic Peptides
  作者：Vincent Aucagne、David A. Leigh、Julia S. Lock、Andrew R. Thomson

  DOI：10.1021/ja057206q

  日期：2006.2.1

  The synthesis of rotaxanes derived from the synthetic peptide macrocycles cyclo(l-ProGly)4 and cyclo(l-ProGly)5 and diammonium threads is described. [2]Rotaxanes are formed in good yields (56-63%), despite the disruption of internal amide-amide hydrogen bonding in the macrocycles.

  描述了衍生自合成肽大环环 (l-ProGly)4 和环 (l-ProGly)5 和二铵线的轮烷的合成。[2] 尽管大环中的内部酰胺-酰胺氢键被破坏，但仍以良好的产率 (56-63%) 形成轮烷。
• Synthesis of N-Peptide-6-Amino-d-Luciferin Conjugates with Optimized Fragment Condensation Strategy
  作者：Anita K. Kovács、Péter Hegyes、Gábor J. Szebeni、Krisztián Bogár、László G. Puskás、Gábor K. Tóth

  DOI：10.1007/s10989-018-9768-8

  日期：2019.9

  The synthesis of peptide-luciferin conjugates has a pivotal role in the development of bioluminescent detection systems that are based on the determination of protease enzyme activity. This work describes the optimized synthesis of an N-peptide-6-amino-d-luciferin conjugate (Fmoc-Gly-Pro-6-amino-d-luciferin) with a simple fragment condensation method in adequate yields. Fmoc-Gly-Pro-6-amino-d-luciferin was produced from a previously synthesized Fmoc-Gly-Pro-OH and also previously synthesized 6-amino-2-cyanobenzothiazole with an optimized method, to which conjugate cysteine was added in an also improved way. The resulting conjugate was successfully used in a bioluminescent system, in vitro, demonstrating the applicability of the method.

  肽-荧光素共轭物的合成在基于蛋白酶活性测定的生物发光检测系统的开发中起着举足轻重的作用。本研究采用简单的片段缩合法优化合成了一种 N-肽-6-氨基-d-荧光素共轭物（Fmoc-Gly-Pro-6-氨基-d-荧光素），产量充足。Fmoc-Gly-Pro-6-amino-d-luciferin 是由之前合成的 Fmoc-Gly-Pro-OH 和之前合成的 6-amino-2-cyanobenzothiazole 通过优化的方法制得的，其中还改进了添加共轭半胱氨酸的方法。所得到的共轭物被成功地用于体外生物发光系统，证明了该方法的适用性。