Volume 22, Issue 25
Isocyclic Compounds
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ChemInform Abstract: Aglycone Fragmentation Accompanies β-Glucosidase-Catalyzed Hydrolysis of Salicortin, a Naturally-Occurring Phenol Glycoside.

T. P. CLAUSEN

T. P. CLAUSEN

Dep. Chem., Univ. Alaska, Fairbanks, AK 99775-0520, USA

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J. W. KELLER

J. W. KELLER

Dep. Chem., Univ. Alaska, Fairbanks, AK 99775-0520, USA

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P. B. REICHARDT

P. B. REICHARDT

Dep. Chem., Univ. Alaska, Fairbanks, AK 99775-0520, USA

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First published: June 25, 1991

Abstract

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ChemInform Abstract

Enzymatic hydrolysis of salicortin (Ia) releases glucose while its aglycone (Ib) is decarboxylated and undergoes an unusual fragmentation- recombination reaction, leading to (IV) via a postulated ortho-quinone methide (II). The decomposition of (Ia) is accompanied by a slow time- dependent irreversible inhibition of the enzyme.

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