5-Benzoyl triazole as new structural dimension in glycoconjugates

• Published in: Carbohydrate research Vol. 469; pp. 23 - 30
• Main Authors: Sahoo, Laxminarayan, Kundu, Soumya, Singhamahapatra, Anadi, Jena, Naresh K., Nayak, Ganesh C., Sahoo, Satyanarayan
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.11.2018; Elsevier
• Subjects: 5-Benzoyl triazole; Biochemistry & Molecular Biology; Carbohydrate Conformation; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; Click reaction; Glycoconjugate; Glycoconjugates - chemistry; Life Sciences & Biomedicine; Models, Molecular; Physical Sciences; Science & Technology; Structural study; Triazoles - chemistry; Structural study; Click reaction; Glycoconjugate; 5-Benzoyl triazole; CLICK CHEMISTRY; AZIDE; DISCOVERY
• ISSN: 0008-6215; 1873-426X; 1873-426X
• DOI: 10.1016/j.carres.2018.08.015

In recent years, 1,4-triazole rings are being widely used for the synthesis of carbohydrate derived biomimetics, due to their easy synthesis and wide range of functional group compatibility. These triazole rings lead to synthetic molecules with improved enzymatic stability, bioavailability, and structural diversity. In this present work, a benzoyl group has been introduced at the C-5 position of the triazole ring present in the synthetic glycoconjugates providing further structural diversity to the molecule. 5-Benzoyl 1,4-triazole ring containing glycoconjugates were synthesized using Cu(I) catalyzed [3 + 2] cycloaddition reaction of per-O-acetylated glycopyranosyl azide and phenyl acetylene followed by in situ electrophilic addition of benzoyl group to the Cu(I) coordinated triazole intermediate. The X-ray crystal structure of one of the 5-benzoyl 1,4-triazole linked glycoconjugate derived from d-xylose {1-N-(2,3,4-tri-O-acetyl-β-d-xylopyranosyl)-4-phenyl-5-benzoyl-1,2,3-triazole} showed unique pattern of intermolecular CH…O interactions arranging the molecules in an anti-parallel orientation. The structure and morphology of the compounds were further explored using computational calculation and scanning electron microscopic (SEM) study which firmly established the uniqueness of 5-benzoyl 1,4-triazole linked glycoconjugates compared to that of 5-H 1,4-triazole linked derivative. [Display omitted] •Single step synthesis of 5-benzoyl triazole linked glycoconjugates using [3 + 2] cycloaddition.•X-Ray crystal structure of one of the derivatives synthesized showed unique antiparallel arrangement of non-covalent interactions and DFT calculations showed good agreement with XRD data.•SEM study of the synthesized derivatives established the uniqueness of 5-benzoyl 1,4-triazole linked glycoconjugates compared to that of 5-H 1,4-triazole linked derivative.