A simple procedure for preparing chitin oligomers through acetone precipitation after hydrolysis in concentrated hydrochloric acid

Nao Kazami; Masayoshi Sakaguchi; Daisuke Mizutani; Tatsuhiko Masuda; Satoshi Wakita; Fumitaka Oyama; Masao Kawakita; Yasusato Sugahara

doi:10.1016/j.carbpol.2015.05.082

A simple procedure for preparing chitin oligomers through acetone precipitation after hydrolysis in concentrated hydrochloric acid

Carbohydr Polym. 2015 Nov 5:132:304-10. doi: 10.1016/j.carbpol.2015.05.082. Epub 2015 Jun 30.

Authors

Nao Kazami¹, Masayoshi Sakaguchi¹, Daisuke Mizutani¹, Tatsuhiko Masuda¹, Satoshi Wakita¹, Fumitaka Oyama¹, Masao Kawakita², Yasusato Sugahara³

Affiliations

¹ Biotechnology Laboratory, Department of Applied Chemistry, Kogakuin University, 2, 665-1 Nakano-cho, Hachioji, Tokyo 192-0015, Japan.
² Biotechnology Laboratory, Department of Applied Chemistry, Kogakuin University, 2, 665-1 Nakano-cho, Hachioji, Tokyo 192-0015, Japan; Center for Medical Research Cooperation, The Tokyo Metropolitan Institute of Medical Science, 1-6 Kamikitazawa, 2-chome, Setagaya-ku, Tokyo 156-8506, Japan.
³ Biotechnology Laboratory, Department of Applied Chemistry, Kogakuin University, 2, 665-1 Nakano-cho, Hachioji, Tokyo 192-0015, Japan. Electronic address: [email protected].

PMID: 26256353
DOI: 10.1016/j.carbpol.2015.05.082

Abstract

Chitin oligomers are of interest because of their numerous biologically relevant properties. To prepare chitin oligomers containing 4-6 GlcNAc units [(GlcNAc)4-6], α- and β-chitin were hydrolyzed with concentrated hydrochloric acid at 40 °C. The reactant was mixed with acetone to recover the acetone-insoluble material, and (GlcNAc)4-6 was efficiently recovered after subsequent water extraction. Composition analysis using gel permeation chromatography and MALDI-TOF mass spectrometry indicated that (GlcNAc)4-6 could be isolated from the acetone-insoluble material with recoveries of approximately 17% and 21% from the starting α-chitin and β-chitin, respectively. The acetone precipitation method is highly useful for recovering chitin oligomers from the acid hydrolysate of chitin. The changes in the molecular size and higher-order structure of chitin during the course of hydrolysis were also analyzed, and a model that explains the process of oligomer accumulation is proposed.

Keywords: Acetone precipitation; Acid hydrolysis; Chitin; Chitin oligomer; Water extraction.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetone / chemistry*
Animals
Chemical Precipitation
Chitin / chemistry*
Decapodiformes / chemistry*
Hydrochloric Acid / chemistry*
Hydrolysis
Oligosaccharides / chemistry*
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

Oligosaccharides
Acetone
Chitin
N-acetylchitohexaose
Hydrochloric Acid