Synthesis of chitin and chitosan stereoisomers by thermostable α-glucan phosphorylase-catalyzed enzymatic polymerization of α-D-glucosamine 1-phosphate

Organic & Biomolecular Chemistry
Jun-Ichi KadokawaKazuya Yamamoto

Abstract

The relationship between two aminopolysaccharide stereoisomers, namely α-(1→4)- and β-(1→4)-linked (N-acetyl)-D-glucosamine polymers, is of significant interest within the field of polysaccharide science, as they correspond to amino analogs of the representative abundant natural polysaccharides, viz. amylose and cellulose. While the latter glucosamine polymer is the basis of well-known natural polysaccharides, chitin and chitosan (linear polysaccharides composed of β-(1→4)-linked N-acetyl-D-glucosamine and D-glucosamine), to the best of our knowledge, the former (α-(1→4)-linked) has not been observed in nature. For the purpose of these studies, the synthesis of such non-natural aminopolysaccharides was performed by the thermostable α-glucan phosphorylase (from Aquifex aeolicus VF5)-catalyzed enzymatic polymerization of α-D-glucosamine 1-phosphate (GlcN-1-P), via successive α-glucosaminylations, in ammonia buffer containing Mg(2+) ions, resulting in the production of the α-(1→4)-linked D-glucosamine polymers, corresponding to the structure of the chitosan stereoisomer. Subsequent N-acetylation of the products gave the aminopolysaccharides, corresponding to the chitin stereoisomer.

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Jul 1, 2014·Macromolecular Bioscience·Yusei TakataJun-Ichi Kadokawa

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Citations

Jan 23, 2016·Chemical Reviews·Shin-ichiro ShodaShiro Kobayashi
Oct 7, 2015·Frontiers in Bioengineering and Biotechnology·Ellis C O'Neill, Robert A Field
Jun 10, 2016·Organic & Biomolecular Chemistry·Takuya NakauchidaJun-Ichi Kadokawa
Aug 11, 2016·Wiley Interdisciplinary Reviews. Nanomedicine and Nanobiotechnology·Tomoki Nishimura, Kazunari Akiyoshi
Jul 26, 2018·Applied Microbiology and Biotechnology·Zorica UbiparipTom Desmet

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