1,5-Disubstituted 1,2,3-Triazole Linked Disaccharides: Metal-Free Syntheses and Screening of a New Class of Ribonuclease A Inhibitors

Publication date: Available online 5 December 2017
Source:Bioorganic & Medicinal Chemistry
Author(s): Anirban Kayet, Dhrubajyoti Datta, Ashrukana Das, Swagata Dasgupta, Tanmaya Pathak
1,5-Regioisomeric triazole linked disccharides have been synthesized and screened for their inhibitory properties against ribonuclease A (RNase A). The angular constraint-driven 'crescent shaped' inhibitors accommodated themselves into the enzyme active site. An improved enzyme inhibition was observed with increased H-bonding ability of polar functional groups in the modified disaccharides. In this series, introduction of two carboxyl groups in the furanose rings elicited the best result with an inhibition constant of 50±3 µM. This is the first ever report on the use of disaccharides as RNase A inhibitors.

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