N-Boc-Gly-L-Ala-pNA | 82518-66-9

• 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: N-Boc-Gly-L-Ala-pNA
• 英文别名: Nα-Boc-Gly-L-Ala-pNA；tert-butyl N-[2-[[(2S)-1-(4-nitroanilino)-1-oxopropan-2-yl]amino]-2-oxoethyl]carbamate
• CAS: 82518-66-9
• 化学式: C₁₆H₂₂N₄O₆
• 分子量: 366.374
• InChiKey: ZUKUNESUXTZEBT-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-Boc-Gly-L-Ala-pNA 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (S)-2-(2-Amino-acetylamino)-N-(4-nitro-phenyl)-propionamide
  参考文献：
  名称：

  Polymer-assisted solution-phase parallel synthesis of dipeptide p-nitroanilides and dipeptide diphenyl phosphonates

  摘要：

  This letter describes the parallel synthesis of dipeptide p-nitroanilides (1) and dipeptide diphenyl phosphonates (2). compounds that can be used as Substrates and irreversible inhibitors for the rapid profiling of dipeptidyl peptidases. A polymer-assisted solution-phase synthesis was used for a rapid and clean Coupling between easily available building blocks. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01954-2
• 作为产物：
  描述：

  L-丙氨酸4-硝基酰苯胺 、 4-guanidinophenyl N-(tert-butoxycarbonyl)glycinate 在 4-morpholinepropanesulfonate buffer 、 methyltrypsin 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 4.0h， 以38%的产率得到N-Boc-Gly-L-Ala-pNA
  参考文献：
  名称：

  Methyltrypsin-Catalyzed Peptide Coupling: Comparison of Alkyl Ester and Guanidinophenyl Ester Derivatives as Acyl Donor Component

  摘要：

  Methyltrypsin-catalyzed peptide synthesis has been studied by using conventional alkyl ester and p-guanidinophenyl ester derivatives of alpha-amino acid as the acyl donor component. They were found to be coupled with alpha-amino acid derivatives (acyl acceptor component) to produce dipeptide. The behavior of methyltrypsin toward both the substrates has been studied. (C) 1997 Academic Press.

  DOI：

  10.1006/bioo.1997.1076

文献信息

• Atlantic Cod Trypsin-Catalyzed Peptide Synthesis with Inverse Substrates as Acyl Donor Components
  作者：Tomoyoshi Fuchise、Hideki Kishimura、Zhi-hong Yang、Mareshige Kojoma、Eiko Toyota、Haruo Sekizaki

  DOI：10.1248/cpb.58.484

  日期：——

  Atlantic cod trypsin-catalyzed peptide synthesis has been studied by using p-amidino- and p-guanidinophenyl esters of N-(tert-butyloxycarbonyl)amino acid as acyl donor components. The reaction temperature was optimized at 0 degrees C. The method was shown to be successful as effectively for synthesizing the peptide and useful for preparing dipeptide between D-amino acid with D-amino acid and beta-amino

  大西洋鳕鱼胰蛋白酶催化的肽合成已通过使用N-（叔丁氧羰基羰基）氨基酸的对-基和对胍基苯基酯作为酰基供体组分进行了研究。反应温度在0摄氏度下进行了优化。该方法成功地合成了肽，成功地用于制备D-氨基酸与D-氨基酸和β-氨基酸与β-氨基酸之间的二肽。 。所得产物的酶水解可忽略不计。
• Trypsin-Catalyzed Synthesis of Dipeptide Containing .ALPHA.-Aminoisobutylic Acid Using p- and m-(Amidinomethyl)phenyl Esters as Acyl Donor
  作者：Haruo Sekizaki、Kunihiko Itoh、Akiyoshi Shibuya、Eiko Toyota、Mareshige Kojoma、Kazutaka Tanizawa

  DOI：10.1248/cpb.56.688

  日期：——

  Two series of inverse substrates, p- and m-(amidinomethyl)phenyl esters derived from N-(tert-butyloxycarbonyl)amino acid, were prepared as acyl donor components for enzymatic peptide synthesis. They were found to be readily coupled with an acyl acceptor such as L-alanine p-nitroanilide to produce dipeptide. An alpha-aminoisobutyric acid containing dipeptide was especially obtained in satisfactory yield

  制备了两种相反的底物，衍生自N-（叔丁氧基羰基）氨基酸的对-和间-（m基甲基）苯基酯，作为用于酶促肽合成的酰基供体组分。发现它们易于与酰基受体如L-丙氨酸对硝基苯胺偶联以产生二肽。尤其以令人满意的产率获得了含有二肽的α-氨基异丁酸。灰链霉菌胰蛋白酶比牛胰蛋白酶更有效。通过改变有机溶剂，pH值和酰基受体浓度研究了偶联反应的最佳条件。发现所得产物的酶水解可忽略不计。
• Trypsin-Catalyzed Peptide Synthesis with Various p-Guanidinophenyl Esters as Acyl Donors.
  作者：Haruo SEKIZAKI、Kunihiko ITOH、Eiko TOYOTA、Kazutaka TANIZAWA

  DOI：10.1248/cpb.44.1585

  日期：——

  Trypsin-catalyzed peptide synthesis has been studied by using p-guanidinophenyl esters of N alpha-(tert-butyloxycarbonyl)amino acid and peptide as acyl donor components. The reaction conditions were optimized for organic solvents, pH, and concentration of acceptor. The method was especially useful for the preparation of various peptides containing D-amino acids. The enzymatic hydrolysis of the resulting

  通过使用Nα-（叔丁氧羰基羰基）氨基酸的对胍基苯基酯和肽作为酰基供体组分，研究了胰蛋白酶催化的肽合成。反应条件针对有机溶剂，pH和受体浓度进行了优化。该方法对于制备各种包含D-氨基酸的肽特别有用。所得产物的酶水解可忽略不计。
• Upon DNP-aromatic Rule. Effect of Chromophore Exchange on the CD Spectra of<i>N</i>-DNP-arylalkylamines
  作者：Masao Kawai、Ukon Nagai

  DOI：10.1246/bcsj.55.1327

  日期：1982.4

  CD spectra of the analogs of aromatic DNP-α-amino acids and the related N-DNP-arylalkylamines, in which the positions of the two chromophoric groups were exchanged with each other, were studied. The analogs, in which the DNP-amino group is separated from the asymmetric carbon, did not show any marked Cotton effect near 400 nm, indicating the importance of direct attachment of the DNP–NH group to the chiral carbon atom for showing the characteristic CD spectra of N-DNP-aromatic α-amino acids.

  对芳香族DNP-α-氨基酸类似物和相关的N-DNP-芳基烷基胺（其中两个发色团的位置相互交换）的CD光谱进行了研究。在DNP-氨基与不对称碳原子分离的类似物中，在400 nm附近没有出现明显的棉花效应，这表明DNP-NH基团直接连接到手性碳原子对于显示N-DNP-芳香族α-氨基酸的特征CD光谱非常重要。
• Application of Inverse Substrates to Trypsin-Catalyzed Peptide Synthesis
  作者：Kunihiko Itoh、Haruo Sekizaki、Eiko Toyota、Norihisa Fujiwara、Kazutaka Tanizawa

  DOI：10.1006/bioo.1996.0007

  日期：1996.3

  Trypsin-catalyzed peptide synthesis has been studied by using ''inverse substrate,'' i.e., p-amidinophenyl ester derived from alpha-amino acid derivative as an acyl donor component. Inverse substrate can afford acyl trypsin in a very specific manner, liberating the site-specific p-amidinophenyl moiety as the leaving group. Thus a variety of alpha-amino acid residues which are a part of p-amidinophenyl ester can be involved in the trypsin-catalyzed coupling reaction. The method has been shown to be successful as expected. In conclusion, the method was proposed as a new procedure which overcomes the disadvantage of enzymatic peptide synthesis. (C) 1996 Academic Press, Inc.