高等学校化学学报 ›› 2022, Vol. 43 ›› Issue (8): 20220134.doi: 10.7503/cjcu20220134

• 有机化学 • 上一篇    下一篇

生物-化学法合成黑色素前体5, 6-二羟基吲哚

金睿明1,2, 穆晓清1,2(), 徐岩1   

  1. 1.江南大学生物工程学院酿造微生物学与应用酶学研究室, 无锡 214122
    2.江南大学产业技术研究院, 宿迁 223800
  • 收稿日期:2022-03-03 出版日期:2022-08-10 发布日期:2022-04-06
  • 通讯作者: 穆晓清 E-mail:xqmu@jiangnan.edu.cn
  • 基金资助:
    国家重点研发计划项目(2021YFC2100100);国家自然科学基金(21336009);高等学校学科创新引智计划(111计划)项目(111-2-06)

Bio-chemical Synthesis of Melanin Precursor—— 5,6-Dihydroxyindole(DHI)

JIN Ruiming1,2, MU Xiaoqing1,2(), XU Yan1   

  1. 1.Lab of Brewing Microbiology and Applied Enzymology,School of Biotechnology,Jiangnan University,Wuxi 214122,China
    2.Jiangnan University Institute of Industrial Technology,Suqian 223800,China
  • Received:2022-03-03 Online:2022-08-10 Published:2022-04-06
  • Contact: MU Xiaoqing E-mail:xqmu@jiangnan.edu.cn
  • Supported by:
    the National Key Research and Development Program of China(2021YFC2100100);the National Natural Science Foundation of China(21336009);the Program of Introducing Talents of Discipline to Universities, China(111-2-06)

摘要:

研究了偶联Saccharomyces cerevisiae BY4741/pYX212?TYR催化L-多巴(L-Dopa)合成多巴色素(DC)的生物氧化步骤和DC还原合成5,6-二羟基吲哚(DHI)化学步骤, 实现了DHI的生物-化学合成. 通过优化生物氧化步骤的反应条件及供氧策略等因素, 使L-Dopa的转化率提升至94.75%; 通过优化化学还原步骤反应条件及化学助剂, 使DHI的产率提高到90.03%. 产物的超高效液相色谱-四极杆飞行时间质谱联用(UPLC-Q-TOF-MS)分析结果表明, 反应体系中存在DHI可溶性低聚物.

关键词: 5, 6-二羟基吲哚, 酪氨酸酶, L-多巴, 多巴色素, 生物-化学合成途径

Abstract:

In this study, the biological oxidation step for the synthesis of dopachrome(DC) from L-3,4-dihydroxyphenylalanine(L-Dopa) catalyzed by Saccharomyces cerevisiae BY4741/pYX212-TYR and the chemical step for the reductive synthesis of 5,6-dihydroxyindole(DHI) from DC were coupled, realizing the bio-chemical synthesis of DHI. By optimizing the reaction conditions and the oxygen supply strategy of the biological oxidation step, the conversion rate of L-Dopa increased to 94.75%; by optimizing the reaction conditions and chemical additives of the chemical reduction step, the yield of DHI increased to 90.03%. Ultra high performance liquid chromatography tandem quadrupole time of flight mass spectroscopy(UPLC-Q-TOF-MS) identification for the products showed that DHI-soluble oligomers existed in the reaction system.

Key words: 5, 6-Dihydroxyindole, Tyrosinase, L-3, 4-Dihydroxyphenylalanine, Dopachrome, Bio-chemical synthesis pathway

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