Boc-Gly-Pro-Gly-Pro-Gly-Pro-OH | 55301-11-6

• 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: Boc-Gly-Pro-Gly-Pro-Gly-Pro-OH
• 英文别名: N-tert-butoxycarbonylglycyl-prolyl-glycyl-prolyl-glycyl-proline；Boc-Gly-Pro-Gly-Pro-Gly-Pro；(2S)-1-[2-[[(2S)-1-[2-[[(2S)-1-[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]pyrrolidine-2-carbonyl]amino]acetyl]pyrrolidine-2-carbonyl]amino]acetyl]pyrrolidine-2-carboxylic acid
• CAS: 55301-11-6
• 化学式: C₂₆H₄₀N₆O₉
• 分子量: 580.638
• InChiKey: MPWBBSDPLQWZOM-BZSNNMDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  195
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Boc-Gly-Pro-Gly-Pro-Gly-Pro-OH 在 sodium methylate 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成
  参考文献：
  名称：

  Amino acid and peptide derivatives of the tylosin family of macrolide antibiotics modified by aldehyde function

  摘要：

  Fourteen new functionally active amino acid and peptide derivatives of the antibiotics tylosin, desmycosin, and 5-O-mycaminosyltylonolide were synthesized in order to study the interaction of the growing polypeptide chain with the ribosomal tunnel. The conjugation of various amino acids and peptides with a macrolide aldehyde group was carried out by two methods: direct reductive amination with the isolation of the intermediate Schiff bases or through binding via oxime using the preliminarily obtained derivatives of 2-aminooxy-acetic acid.

  DOI：

  10.1134/s1068162010020159
• 作为产物：
  描述：

  BOC-甘氨酸 在 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 生成 Boc-Gly-Pro-Gly-Pro-Gly-Pro-OH
  参考文献：
  名称：

  Amino acid and peptide derivatives of the tylosin family of macrolide antibiotics modified by aldehyde function

  摘要：

  Fourteen new functionally active amino acid and peptide derivatives of the antibiotics tylosin, desmycosin, and 5-O-mycaminosyltylonolide were synthesized in order to study the interaction of the growing polypeptide chain with the ribosomal tunnel. The conjugation of various amino acids and peptides with a macrolide aldehyde group was carried out by two methods: direct reductive amination with the isolation of the intermediate Schiff bases or through binding via oxime using the preliminarily obtained derivatives of 2-aminooxy-acetic acid.

  DOI：

  10.1134/s1068162010020159

文献信息

• Peptide derivatives of tylosin-related macrolides
  作者：G. A. Korshunova、N. V. Sumbatyan、N. V. Fedorova、I. V. Kuznetsova、A. V. Shishkina、A. A. Bogdanov

  DOI：10.1134/s1068162007020033

  日期：2007.3

  Approaches to the synthesis of model compounds based on the tylosin-related macrolides desmycosin and O=mycaminosyltylonolide were developed to study the conformation and topography of the nascent peptide chain in the ribosome tunnel using specially designed peptide derivatives of macrolide antibiotics. A method for selective bromoacetylation of desmycosin at the hydroxyl group of mycinose was developed

  开发了基于泰乐菌素相关的大环内酯类去霉素和 O=mycaminosyltylonolide 的模型化合物的合成方法，以使用专门设计的大环内酯类抗生素的肽衍生物研究核糖体隧道中新生肽链的构象和形貌。开发了一种在mycinose 羟基上选择性溴乙酰化脱粘菌素的方法，该方法涉及mycaminose 的初步乙酰化。抗生素的 4″-溴乙酰基衍生物与二肽 Boc-Ala-Ala-OH 和六肽 MeOTr-Gly-Pro-Gly-Pro-Gly-Pro-OH 的铯盐反应生成相应的肽衍生物去霉菌素。受保护的肽 Boc-Ala-Ala-OH、Boc-Ala-Ala-Phe-OH 和 Boc-Gly-Pro-Gly-Pro-Gly-Pro-OH 与 O-mycaminosyltylonolide 的 C23-羟基缩合。
• Structural-functional study of glycine-and-proline-containing peptides (Glyprolines) as potential neuroprotectors
  作者：K. V. Martynova、L. A. Andreeva、P. A. Klimova、Yu. G. Kirillova、V. P. Shevchenko、I. Yu. Nagaev、S. I. Shram、V. I. Shvets、N. F. Myasoedov

  DOI：10.1134/s1068162009020022

  日期：2009.3

  A synthetic scheme for preparation of (Gly-Pro) (n) , (Pro-Gly) (n) (n = 2, 3), and (Pro-Gly-Pro) (n) (n = 1, 2) peptides was elaborated. The effect of the synthesized peptides and the Gly-Pro and Pro-Gly dipeptides on survival of cultured cells of PC12 rat pheochromocytoma was studied under the conditions of oxidative stress induced by brief incubation of the cells with hydrogen peroxide. Peptides of the general formula (Gly-Pro) (n) and the Pro-Gly-Pro peptide at a concentration of 0.2-100 mu M were shown to decrease the number of damaged cells. The Gly-Pro peptide was the most active and decreased the number of damaged cells by 49% on average at a concentration of 100 mu M.