Please use this identifier to cite or link to this item: https://doi.org/10.1021/bm049672y
Title: Preparation of C-6 substituted chitin derivatives under homogeneous conditions
Authors: Zou, Y.
Khor, E. 
Issue Date: Jan-2005
Source: Zou, Y., Khor, E. (2005-01). Preparation of C-6 substituted chitin derivatives under homogeneous conditions. Biomacromolecules 6 (1) : 80-87. ScholarBank@NUS Repository. https://doi.org/10.1021/bm049672y
Abstract: Tosylation of chitin under homogeneous conditions was achieved by the reaction of tosyl chloride with chitin in a DMAc/LiCl solvent system. The resultant tosyl - chitin was fully N-acetylated with acetic anhydride in methanol. The fully acetylated tosyl - chitin was subsequently reacted with the sodium salts of ethyl p-hydroxybenzoate, diethyl malonate, and diethyl phosphite in DMAc to give the corresponding chitin derivatives of 6-O-ethyl benzoate - chitin, 6-deoxy-diethyl malonate - chitin, and 6-(deoxydiethyl) phosphite - chitin, respectively. Subsequent hydrolysis of the chitin - ester derivatives with tert-butoxide in dimethyl sulfoxide (DMSO) generated 6-O-carboxyphenyl - chitin and 6-(deoxydicarboxy)methyl - chitin. The structures of the chitin derivatives were assessed by FT-IR, 13C NMR, and 31P NMR, while the degree of substitution of the SN2 reaction was estimated by elemental analysis. All the chitin derivatives were found to be soluble or swellable in water, DMAc, or DMSO. © 2005 American Chemical Society.
Source Title: Biomacromolecules
URI: http://scholarbank.nus.edu.sg/handle/10635/94602
ISSN: 15257797
DOI: 10.1021/bm049672y
Appears in Collections:Staff Publications

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