Boc-Gly-Aib2-OH | 144183-24-4

• 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-Aib2-OH
• CAS: 144183-24-4
• 化学式: C₁₅H₂₇N₃O₆
• 分子量: 345.396
• InChiKey: UMIXKXYSJISGKE-UHFFFAOYSA-N

物化性质

• 沸点：
  620.2±50.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.39
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  133.83
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Boc-Gly-Aib2-OH 在 盐酸 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 Ac-Gly-Aib2-Gly-L-Ser(COAQ)-OMe
  参考文献：
  名称：

  Intramolecular photoreaction of synthetic oligopeptide-linked anthraquinone molecules

  摘要：

  Photoreaction of (N-acetylglycyl)oligopeptide-linked anthraquinone molecules was investigated. In an acetonitrile site of glycine residue. The biradical formed was followed by the formation of C-O bonding via radical recombination to produce ring-closure products in high yields (23-58%). A variety of oligopeptide spacers between acetylglycine and anthraquinone moieties were systematically changed, and their photoreactivities were investigated. The isolated ring-closure products showed a site-selectivity in the photoreaction; one of the carbonyl groups of anthraquinone moiety coupled with the methylene group predominantly (the selectivity was 88/12-100/0). The efficiency of the photocyclization was dependent upon the size and the sequence of the oligopeptide spacer. These results showed that the oligopeptide spacer might control the distance and the orientation among the reaction sites, glycine methylene, and anthraquinone carbonyl groups.

  DOI：

  10.1021/jo00049a019

文献信息

• Intramolecular Photocyclization in Quinone-Bearing Oligopeptides
  作者：Hitoshi Tamiaki、Masakazu Hashimoto、Kazuhiro Maruyama

  DOI：10.1246/bcsj.67.1987

  日期：1994.7

  The photoexcited anthraquinone moiety (AQ) of (N-acetylglycyl)oligopeptide-linked anthraquinones in acetonitrile abstracted intramolecularly the hydrogen in the α-methylene of glycine to give a sole isomeric ring-closure product. Site-selectivity was produced mainly by a difference in the spatial distance between the C=O of AQ and reactive CH2.

  在乙腈中，(N-乙酰基甘氨酰)寡肽连接的蒽醌的蒽醌部分(AQ)被光激发后，从甘氨酸的α-亚甲基内部抽取氢，生成唯一的异构环化产物。这种位点选择性主要是由于AQ的C=O与反应性CH2之间的空间距离差异所导致的。