Critical role of Bronsted acid in Lewis-acid catalyzed synthesis of Amadori and Heyns compounds of β-amino acids.

Debashree, Chanda and Gangothri, M. Venkataswamy and Lagamawwa, V. Hipparagi and Nanishankar, V. Harohally (2021) Critical role of Bronsted acid in Lewis-acid catalyzed synthesis of Amadori and Heyns compounds of β-amino acids. Synthetic Communications, 51 (22). pp. 3379-3389.

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Abstract

Amadori and Heyns rearrangement reactions are a century old reac�tions of the carbohydrates. The great body of literature on these reac�tions are concentrated on A-amino acids. Reports on the synthesis and chemistry of Amadori and Heyns compounds derived from b-amino acids are scarce. We demonstrate herein, via Lewis-acid catalysis, synthesis of Amadori and Heyns compounds derived from b-amino acids consisting of b-alanine and b-phenylalanine with, D-xylose, D-galactose, D-fructose, D-mannose, D-maltose, D-lactose. The accomplished Lewis-acid catalyzed method is practical and devoid of separation techniques for achieving purity. We also report insight on the mechanism of Lewis-acid catalyzed Amadori and Heyns rearrangement reactions, and reveal the key role of Bronsted acid in Lewis-acid catalyzed Amadori and Heyns synthesis of b-amino acids.

Item Type:	Article
Uncontrolled Keywords:	Amadori reaction; Heyns reaction; b-amino acids; Lewis acid; Bronsted acid; Catalysis
Subjects:	500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 03 Amino Acid Chemistry
Divisions:	Plantation Products Spices and Flavour Technology
Depositing User:	Food Sci. & Technol. Information Services
Date Deposited:	16 May 2023 04:30
Last Modified:	16 May 2023 04:30
URI:	http://ir.cftri.res.in/id/eprint/16352

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