title: Chemical modification of chitosan. Part 15: synthesis of novel chitosan derivatives by substitution of hydrophilic amine using N-carboxyethylchitosan ethyl ester as an intermediate.
abstract: The Michael type reaction of chitosan with ethyl acrylate has been investigated. Although this reaction was quite slow in the case of chitosan, the reiteration of the reaction was an effective means for increasing the degree of substitution (DS) of ethyl ester. The N-carboxyethylchitosan ethyl ester as an intermediate was successfully substituted with various hydrophilic amines, although the simultaneous hydrolysis of the ester to carboxylic acid also occurred. Water-soluble chitosan derivatives were obtained by substitution with hydroxyalkylamines and diamines.
authors.affiliation: Green Biotechnology Research Group, The Special Division for Human Life Technology, National Institute of Advanced Industrial Science and Technology, 1-8-31 Midorigaoka, Ikeda, 563-8577, Osaka, Japan.
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Sashiwa
authors.forename: Norioki
authors.initials: N
authors.lastname: Kawasaki
authors.forename: Atsuyoshi
authors.initials: A
authors.lastname: Nakayama
authors.forename: Einosuke
authors.initials: E
authors.lastname: Muraki
authors.forename: Hirofumi
authors.initials: H
authors.lastname: Yajima
authors.forename: Naoki
authors.initials: N
authors.lastname: Yamamori
authors.forename: Yoshifumi
authors.initials: Y
authors.lastname: Ichinose
authors.forename: Junzo
authors.initials: J
authors.lastname: Sunamoto
authors.forename: Sei-ichi
authors.initials: S
authors.lastname: Aiba
mesh_terms: D000179:Acrylates / Q000737:chemistry; D000588:Amines / Q000737:chemistry; D002686:Chitin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D048271:Chitosan / Q000031:analogs & derivatives; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D012995:Solubility; D014867:Water / Q000737:chemistry
chemical_list: D000179:Acrylates; D000588:Amines; D004952:Esters; C480500:N-carboxyethylchitosan ethyl ester; D014867:Water; D002686:Chitin; C040833:ethyl acrylate; D048271:Chitosan