Ac-Gly-L-Ser-OMe | 144183-19-7

• 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: Ac-Gly-L-Ser-OMe
• 英文别名: methyl (2S)-2-[(2-acetamidoacetyl)amino]-3-hydroxypropanoate
• CAS: 144183-19-7
• 化学式: C₈H₁₄N₂O₅
• 分子量: 218.21
• InChiKey: JCFXVRFUSBLQHM-LURJTMIESA-N

物化性质

• 沸点：
  558.4±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ac-Gly-L-Ser-OMe 、 蒽醌-2-甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到Ac-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
• 作为产物：
  描述：

  乙酰基甘氨酸 N-羟基丁二酰亚胺酯 、 L-丝氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以93%的产率得到Ac-Gly-L-Ser-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 photoreaction of synthetic oligopeptide-linked anthraquinone molecules
  作者：Kazuhiro Maruyama、Masakazu Hashimoto、Hitoshi Tamiaki

  DOI：10.1021/jo00049a019

  日期：1992.11

  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.