Synthesis and reduction of azidodeoxy derivatives of chitin

Ken-ichi Furuhata, Norihiro Arai, Satoshi Ishizuka, How Tseng, Munenori Sakamoto

Research output: Contribution to journalArticle

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Abstract

Azidodeoxychitin samples were obtained in the reactions of bromodeoxychitin and chlorodeoxychitin samples with sodium azide in polar aprotic solvents. A kinetic equation for a bimolecular reversible reaction was applicable to the azidation of 6-bromo-6-deoxychitin. The rate constant for the exchange with azide ion and the equilibrium constant were 7.36X 10-'M-1 min-' and 57.0 at 50•Ž, respectively, in the binary solvent system of lithium bromide and N,N-dimethylacetamide while they were 88.5 X 10-3 M-'min-' and 0.37, respectively, for the reaction at 60•Ž in methyl sulfoxide. The exchange with azide ion was
slower in the case of 6-chloro-6-deoxychitin samples. Azidodeoxychitin samples were reduced with sodium borohydride in methyl sulfoxide for 24 h at 60'C. Azido groups were consumed almost completely and the selectivity for the reduction to amino groups was higher than 80%.
Original languageEnglish
Pages (from-to)647-653
JournalSen'i Gakkaishi
Volume54
Publication statusPublished - 1998

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sulfoxide
Chitin
Azides
Ion exchange
Sodium
Ions
Derivatives
Sodium Azide
Equilibrium constants
Rate constants
Lithium
Kinetics

Cite this

Furuhata, K., Arai, N., Ishizuka, S., Tseng, H., & Sakamoto, M. (1998). Synthesis and reduction of azidodeoxy derivatives of chitin. Sen'i Gakkaishi, 54, 647-653.

Synthesis and reduction of azidodeoxy derivatives of chitin. / Furuhata, Ken-ichi ; Arai, Norihiro ; Ishizuka, Satoshi; Tseng, How; Sakamoto, Munenori .

In: Sen'i Gakkaishi, Vol. 54, 1998, p. 647-653.

Research output: Contribution to journalArticle

Furuhata, K, Arai, N, Ishizuka, S, Tseng, H & Sakamoto, M 1998, 'Synthesis and reduction of azidodeoxy derivatives of chitin', Sen'i Gakkaishi, vol. 54, pp. 647-653.
Furuhata K, Arai N, Ishizuka S, Tseng H, Sakamoto M. Synthesis and reduction of azidodeoxy derivatives of chitin. Sen'i Gakkaishi. 1998;54:647-653.
Furuhata, Ken-ichi ; Arai, Norihiro ; Ishizuka, Satoshi ; Tseng, How ; Sakamoto, Munenori . / Synthesis and reduction of azidodeoxy derivatives of chitin. In: Sen'i Gakkaishi. 1998 ; Vol. 54. pp. 647-653.
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AB - Azidodeoxychitin samples were obtained in the reactions of bromodeoxychitin and chlorodeoxychitin samples with sodium azide in polar aprotic solvents. A kinetic equation for a bimolecular reversible reaction was applicable to the azidation of 6-bromo-6-deoxychitin. The rate constant for the exchange with azide ion and the equilibrium constant were 7.36X 10-'M-1 min-' and 57.0 at 50•Ž, respectively, in the binary solvent system of lithium bromide and N,N-dimethylacetamide while they were 88.5 X 10-3 M-'min-' and 0.37, respectively, for the reaction at 60•Ž in methyl sulfoxide. The exchange with azide ion wasslower in the case of 6-chloro-6-deoxychitin samples. Azidodeoxychitin samples were reduced with sodium borohydride in methyl sulfoxide for 24 h at 60'C. Azido groups were consumed almost completely and the selectivity for the reduction to amino groups was higher than 80%.

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