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Lewis-Acid-Catalyzed Synthesis of Amadori and Heyns Dipeptides.

Debasree, Chanda and Venkataswamy, Gangothri M. and Nanishankar, V. Harohally (2020) Lewis-Acid-Catalyzed Synthesis of Amadori and Heyns Dipeptides. ChemistrySelect, 5. pp. 12960-12964.

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Abstract

Amadori and Heyns reactions are milestone reactions of carbohydrate chemistry. There have been little efforts in transforming these rearrangement reactions to useful catalytic tools. We demonstrate herein, synthesis of Amadori and Heyns dipeptides via Lewis acid-catalysis. The accomplished catalytic Amadori and Heyns synthesis is devoid of protection and deprotection steps either for dipeptides or for reducing sugar. By the developed catalytic method we achieved, tagatose Amadori dipeptides via reaction of D-galactose with dipeptides including L-alanyl glycine, L-alanyl-L-alanine, L-alanyl-L-glutamine, glycyl-L-phenylalanine, L-leucyl glycine, L-pheynylalanylL-valine in excellent yield. In addition, Heyns dipeptides were also achieved by employing D-fructose and dipeptides consisting of L-alanyl glycine, L-alanyl-L-alanine, L-alanyl-L-glutamine, glycyl-L-phenylalanine, L-leucyl glycine. The realized Lewis acid mediated catalytic method is practical, quantitative, and avoids chromatographic separation techniques.

Item Type: Article
Uncontrolled Keywords: Amadori, Heyns reactions, dipeptides, Lewis acid-catalysis
Subjects: 500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 25 Peptide Chemistry
600 Technology > 08 Food technology > 01 Analysis
Divisions: Plantation Products Spices and Flavour Technology
Depositing User: Food Sci. & Technol. Information Services
Date Deposited: 01 Feb 2021 08:50
Last Modified: 01 Feb 2021 08:50
URI: http://ir.cftri.com/id/eprint/14776

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