Catalytic Depolymerization of Chitin with Retention of N-Acetyl Group
Catalytic Depolymerization of Chitin with Retention of N-Acetyl Group
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DOI：
10.1002/cssc.201501224
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发表时间：
2015-11-23
期刊：
影响因子：
8.4
通讯作者：
Fukuoka, Atsushi
中科院分区：
文献类型：
--
作者：
Yabushita, Mizuho;Kobayashi, Hirokazu;Fukuoka, Atsushi
甲壳素是一种具有-1,4-糖苷键的n -乙酰氨基葡萄糖单元的聚合物，是最丰富的海洋生物质。含有n -乙酰基的几丁质单体是各种精细化学品和药物的有用前体。然而，强健的几丁质选择性转化为n -乙酰化单体目前需要大量过量的酸或较长的反应时间，这限制了它的应用。通过机械化学和均相催化的结合，我们证明了甲壳素快速催化转化为保留n -乙酰基的单体。在H2SO4的催化下，机械力辅助甲壳素解聚得到可溶性短链低聚物。随后的球磨样品水解得到的n -乙酰氨基葡萄糖收率为53%，甲醇水解得到的1- o -甲基- n -乙酰氨基葡萄糖收率高达70%。与传统工艺相比，我们的工艺可以大大减少酸的使用。
Chitin, a polymer of N-acetylglucosamine units with -1,4-glycosidic linkages, is the most abundant marine biomass. Chitin monomers containing N-acetyl groups are useful precursors to various fine chemicals and medicines. However, the selective conversion of robust chitin to N-acetylated monomers currently requires a large excess of acid or a long reaction time, which limits its application. We demonstrate a fast catalytic transformation of chitin to monomers with retention of N-acetyl groups by combining mechanochemistry and homogeneous catalysis. Mechanical-force-assisted depolymerization of chitin with a catalytic amount of H2SO4 gave soluble short-chain oligomers. Subsequent hydrolysis of the ball-milled sample provided N-acetylglucosamine in 53% yield, and methanolysis afforded 1-O-methyl-N-acetylglucosamine in yields of up to 70%. Our process can greatly reduce the use of acid compared to the conventional process.