Bba-Gly-Gly-OMe | 356570-60-0

• 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: Bba-Gly-Gly-OMe
• 英文别名: N-(4-bromobenzyl-1-carbonyl)-glycyl-glycine methyl ester；N-(p-bromobenzoyl)glycylglycine methyl ester；Methyl 2-[[2-[(4-bromobenzoyl)amino]acetyl]amino]acetate
• CAS: 356570-60-0
• 化学式: C₁₂H₁₃BrN₂O₄
• mdl: MFCD12563207
• 分子量: 329.15
• InChiKey: NFTHLHFMOJOBAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Bba-Gly-Gly-OMe 在 lithium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以90.7%的产率得到N-(4-bromobenzyl-1-carbonyl)-glycyl-glycine
  参考文献：
  名称：

  Neutral Peptide Biradicals Formed by Dissociative Electron Transfer

  摘要：

  [GRAPHICS]A new method for the generation of transient neutral biradicals in liquid solution is reported. Photoinduced electron transfer in aqueous solution of the structures shown above leads to neutral biradicals with peptide spacers. Exchange interactions were measured using time-resolved electron paramagnetic resonance (TREPR) and found to be large for the biradicals possessing two and three glycine residue spacers, These findings are compared to previous results from alkyl spaced biradicals of similar chain length.

  DOI：

  10.1021/ol0160452
• 作为产物：
  描述：

  N-(4-bromobenzoyl)glycine methyl ester 在 4-二甲氨基吡啶 氢氧化钾 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 生成 Bba-Gly-Gly-OMe
  参考文献：
  名称：

  Neutral Peptide Biradicals Formed by Dissociative Electron Transfer

  摘要：

  [GRAPHICS]A new method for the generation of transient neutral biradicals in liquid solution is reported. Photoinduced electron transfer in aqueous solution of the structures shown above leads to neutral biradicals with peptide spacers. Exchange interactions were measured using time-resolved electron paramagnetic resonance (TREPR) and found to be large for the biradicals possessing two and three glycine residue spacers, These findings are compared to previous results from alkyl spaced biradicals of similar chain length.

  DOI：

  10.1021/ol0160452

文献信息

• Synthesis and structural characterization of amino acid and peptide derivatives featuring N-(p-bromobenzoyl) substituents as promising connection unit for bio-inspired hybrid compounds
  作者：Frank Eißmann、Edwin Weber

  DOI：10.1016/j.molstruc.2011.03.058

  日期：2011.5

  Abstract Using a sequence of activation, blocking and peptide coupling procedures, a series of ten amino acid and peptide derivatives 1–6 (a, b, respectively) featuring a p-bromobenzoyl substituent attached to the amino group of the parent compound has been synthesized. X-ray crystal structures of two corresponding amino acid (1a, 1b), two amino acid ester (3a, 3b) and three peptide ester derivatives

  摘要 使用一系列活化、封闭和肽偶联程序，合成了一系列十种氨基酸和肽衍生物 1-6（分别为 a、b），其特征是在母体化合物的氨基上有一个对溴苯甲酰基取代基。 . 报道了两种相应氨基酸(1a, 1b)、两种氨基酸酯(3a, 3b)和三种肽酯衍生物(4a, 4b, 5b)的X射线晶体结构，分子的酰胺和肽键均平面和反式配置。分子内相互作用主导着包装基序，从而导致形成链（1a、3a、3b、4a、4b）、分子对（1b）或片层（5b）源自 N-H⋯O 接触，进一步辅助O-H⋯O 和较弱的 C-H⋯O 相互作用，而涉及溴的接触是次要的。
• N-(p-Ethynylbenzoyl) derivatives of amino acid and dipeptide methyl esters – Synthesis and structural study
  作者：Frank Eißmann、Edwin Weber

  DOI：10.1016/j.molstruc.2011.08.034

  日期：2011.11

  N-(p-ethynylbenzoyl) derivatives (1–4) of the amino acids glycine and l -alanine as well as the dipeptides glycylglycine and l -alanylglycine has been synthesized via a two-step reaction sequence including the reaction of an appropriate N-(p-bromobenzoyl) precursor with trimethylsilylacetylene followed by deprotection of the trimethylsilyl protecting group, respectively. X-ray crystal structures of the amino acid

  摘要 通过两步反应序列合成了一系列氨基酸甘氨酸和 l-丙氨酸的 N-(对乙炔基苯甲酰基)衍生物 (1-4) 以及二肽甘氨酰甘氨酸和 l-丙氨酰甘氨酸一个合适的 N-（对溴苯甲酰基）前体与三甲基甲硅烷基乙炔，然后分别对三甲基甲硅烷基保护基进行脱保护。报告了氨基酸和二肽甲酯 1-4 的 X 射线晶体结构。每个分子结构内的酰胺键和肽键都是平面的，并采用反式构型。堆积结构受 NH⋯O 相互作用控制，导致形成特征链基序。更弱的 CH⋯O 和 CH⋯π 接触导致进一步稳定。
• Neutral Peptide Biradicals Formed by Dissociative Electron Transfer
  作者：Colin S. Burns、Lakecia Rochelle、Malcolm D. E. Forbes

  DOI：10.1021/ol0160452

  日期：2001.7.1

  [GRAPHICS]A new method for the generation of transient neutral biradicals in liquid solution is reported. Photoinduced electron transfer in aqueous solution of the structures shown above leads to neutral biradicals with peptide spacers. Exchange interactions were measured using time-resolved electron paramagnetic resonance (TREPR) and found to be large for the biradicals possessing two and three glycine residue spacers, These findings are compared to previous results from alkyl spaced biradicals of similar chain length.