13C CP/MAS NMR Spectral Analysis of 6-O-Tosyl, 6-Deoxy-6-iodo, and 6-Deoxy Derivatives of N-Acetylchitosan in a Solid State

6-O-Tosyl (1, d.s. 0.94, 80% yield), 6-deoxy-6-iodo (2, d.s. 0.49, 86% yield) and 6-deoxy (3, d.s. 0.49, 50% yield) derivatives of N-acetylchitosan were prepared, and a 13 C CP/MAS NMR spectral analysis was performed because no suitable solvent for 3 was found. The 13 C signal for CH 3 at C-6 in 3 w...

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Published inBioscience, biotechnology, and biochemistry Vol. 58; no. 10; pp. 1906 - 1908
Main Authors Zhang, Min, Hisamori, Hiroki, Yamada, Toshihide, Hirano, Shigehiro
Format Journal Article
LanguageEnglish
Published Tokyo Taylor & Francis 01.01.1994
Japan Society for Bioscience Biotechnology and Agrochemistry
Subjects
Analytical, structural and metabolic biochemistry
Biological and medical sciences
Enzymes and enzyme inhibitors
Fundamental and applied biological sciences. Psychology
Hydrolases
Chitinase
Enzyme
Chitin
NMR spectrometry
Substrate
Glycosidases
Substrate specificity
Hydrolases
Chitosan
O-Glycosidases
Derived product
Lysozyme
Structural analysis
Conformation
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Summary:6-O-Tosyl (1, d.s. 0.94, 80% yield), 6-deoxy-6-iodo (2, d.s. 0.49, 86% yield) and 6-deoxy (3, d.s. 0.49, 50% yield) derivatives of N-acetylchitosan were prepared, and a 13 C CP/MAS NMR spectral analysis was performed because no suitable solvent for 3 was found. The 13 C signal for CH 3 at C-6 in 3 was detected at 18.9 ppm, and that for C-4 in 1-3 appeared at 72.2-72.7 ppm, which is in a higher magnetic field than those (82.5-86.0 ppm) in N-acetylchitosan, 6-O- (ethylthio), 6-O-(benzylthio)- and 6-O-(methylthio)-thiocarbonyl derivatives, chitosan, and chitin. This strongly suggests a different molecular conformation for 1-3.
ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.58.1906