methyl N-<2-(N-benzyloxycarbonyl)aminoethyl>glycinate | 128421-96-5

• 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: methyl N-<2-(N-benzyloxycarbonyl)aminoethyl>glycinate
• 英文别名: methyl N-(2-benzyloxycarbonylaminoethyl)glycinate；Z-Gly-ψ(CH2NH)-Gly-OMe；Z-Aeg(H)-OMe；N-(β-Benzyloxycarbonylaminoethyl)glycin-methylester；Methyl 2-[2-(phenylmethoxycarbonylamino)ethylamino]acetate
• CAS: 128421-96-5
• 化学式: C₁₃H₁₈N₂O₄
• 分子量: 266.297
• InChiKey: UUWFWHCPZXXPIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl N-<2-(N-benzyloxycarbonyl)aminoethyl>glycinate 在 lithium hydroxide 、 四(三苯基膦)钯 、 bromo-tris-dimethylamino-phosphonium hexafluorophosphate 、 溶剂黄146 、 二乙胺 、 三乙胺 、 镉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.5h， 生成 {2-[2-([2-(2-Amino-6-benzyloxy-purin-9-yl)-acetyl]-{2-[2-(2-benzyloxycarbonylamino-ethylamino)-acetylamino]-ethyl}-amino)-acetylamino]-ethylamino}-acetic acid methyl ester
  参考文献：
  名称：

  Liquid-phase synthesis of polyamide nucleic acids (PNA)

  摘要：

  Three liquid-phase processes for the elaboration of short orthogonally protected PNA have been devised. Two of these methods are similar to the convergent and divergent approaches in peptide synthesis. The third process consists in building a fully protected polyamide backbone, by using as many different and orthogonal protecting groups as there are different types of nucleic bases in the targeted polyPNA. Simultaneous and selective cleavage of one kind of protecting group allows the simultaneous attachment of several identical nucleobase units. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01211-3
• 作为产物：
  描述：

  2-[Phenylmethoxycarbonyl-[2-(phenylmethoxycarbonylamino)ethyl]amino]acetic acid 在 盐酸 、 氯化亚砜 作用下， 反应 4.5h， 生成 methyl N-<2-(N-benzyloxycarbonyl)aminoethyl>glycinate
  参考文献：
  名称：

  Building units for N-backbone cyclic peptides. 1. Synthesis of protected N-(.omega.-aminoalkylene)amino acids and their incorporation into dipeptide units

  摘要：

  A variety of new amino acids which contain an omega-aminoalkylene group on the N(alpha)-amino nitrogen were synthesized by alkylation of alkylenediamines with alpha-halogeno acids. The reaction proceeds with inversion of configuration; thus, optically pure products were obtained when optically active a-halogeno acids were used. The N-(omega-aminoalkylene)amino acids were protected by orthogonal protecting groups to allow their incorporation into dipeptides by the "solution" techniques and into peptides by the solid-phase peptide synthesis (SPPS) methodology. A series of dipeptide analogs of Phe-Gly, Leu-Gly, Trp-Gly, Phe-Leu, and Phe-Ala in which the nitrogen of the peptide bond is alkylated by omega-aminoalkylene chains with various lengths were prepared. These new protected N-(omega-aminoalkylene)amino acids and their derived dipeptide units may be used as building blocks for conformationally constrained N-backbone cyclic peptides.

  DOI：

  10.1021/jo00047a022

文献信息

• Liquid phase synthesis of a peptidic nucleic acid dimer
  作者：Audrey Farèse、Nadia Patino、Roger Condom、Sandrine Dalleu、Roger Guedj

  DOI：10.1016/0040-4039(96)00037-8

  日期：1996.2

  The first liquid phase synthesis of a peptidic nucleic acid (PNA_) dimer containing guinine and adenine has been achieved in good yields. A new strategy was elaborated in order to circumvent difficult coupling of the protected PNA.

  已经以良好的产率实现了包含精氨酸和腺嘌呤的肽核酸（PNA_）二聚体的第一液相合成。为了避开受保护的PNA的困难耦合，制定了新的策略。
• An improved method for the preparation of desoxopeffides—reductions of endothiopeptides
  作者：Frank S. Guziec、Loide Mayer Wasmund

  DOI：10.1016/s0040-4039(00)94324-7

  日期：1990.1

  Three new procedures for the synthesis of desoxopeptides from endothiopeptides are reported: 1) Raney nickel desulfurizafion, 2) alkylation with triethyloxonium tetrafluoroborate followed by sodium borohydride reduction, and 3) nickel boride reduction. Of these three, reduction with nickel boride was found to be superior due to high yields, reproducibility and convenience.

  从内硫肽合成脱氧肽的三种新方法已有报道：1）阮内镍脱​​硫基硫脲； 2）四氟硼酸三乙基氧鎓烷基化，然后硼氢化钠还原； 3）硼化镍还原。在这三种方法中，由于高收率，可重复性和便利性，发现用硼化镍还原效果更好。
• Improved Large-Scale Liquid-Phase Synthesis and High-Temperature NMR Characterization of Short ­(F-)PNAs
  作者：Tobias A. Plöger、Günter von Kiedrowski

  DOI：10.1002/hlca.201100243

  日期：2011.11

  unpaired PNA n‐mers exist in a mixture of 2n conformers undergoing slow exchange and leading to complicated NMR spectra. Structure analysis was improved by recording 1H‐ and 13C‐NMR spectra at elevated temperatures above the coalescence point. Fully protected backbone derivatives show sharp resonances where expected, and spectra of protected PNAs are remarkably simplified, thereby allowing an interpretation

  我们报告了F-PNA三聚体10和PNA三聚体11的大规模合成。关键的改进是（2,4-二氟-5-甲基苯基）乙酸的简便两步合成（2）。相应的F-PNA低聚物10的水溶性是通过合成溶解度增强剂5a来实现的，该增强剂具有两个带正电且仅由PNA固有的结构元素组成。受保护且未配对的PNA n单体存在于2 n个构象异构体的混合物中，它们经历缓慢交换并导致复杂的NMR光谱。通过记录1 H-和13改进了结构分析高于聚结点的高温下的C-NMR谱图。完全受保护的主链衍生物在预期的地方显示出剧烈的共振，并且受保护的PNA的光谱显着简化，从而首次得以解释。修剪器10和11都被视为基于PNA的自我复制系统的构建块。
• WO2019183577A5
  申请人：——

  公开号：WO2019183577A5

  公开（公告）日：2024-05-13
• N-Aminoalkylpolyglycine. Synthesis, antibacterial activity, and electrochemical behavior as a titrant of living cells
  作者：Eleonora Santucci、Marcello Marchetti、Franco Alhaique、Claudio Botre、Fulvio M. Riccieri

  DOI：10.1021/jm00299a012

  日期：1970.9