The Tohoku Journal of Experimental Medicine
Online ISSN : 1349-3329
Print ISSN : 0040-8727
ISSN-L : 0040-8727
Biochemical Studies on Carbohydrates
CLXXVI. Analysis of Mutarotation of N-Glycosides Second Paper On Aniline-N-riboside
Shigeru Tsuiki
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1955 Volume 61 Issue 4 Pages 365-379

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Abstract
1. Two isomers of different [α]D values (I and II) of aniline-N-riboside were prepared after Berger & Lee and their mutarotations in various solvents were investigated as to the reaction mechanisms to which they owe.
2. The mutarotations in methanol and 0.01 N NaOH are considered as due to rapid isomerization of α β type and slow Schiff base formation.
3. At pH 9.6 the riboside scarcely shows rotation change. Most probably no molecular rearrangement nor scission takes place.
4. Mutarotations of the riboside at pH 5.6 and 7.0 are combined results of anomerization, Schiff base formation and hydrolysis.
5. The more dextrorotatory isomer (I) is assumed as aniline-N-α-ribopyranoside and the less dextrorotatory (II) as aniline-N-β-ribopyrano-side.
Through the Grant Committee for Scientific researches the Education Department gave a grant in aid to us, which is gratefully acknowledged.
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© Tohoku University Medical Press
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