Synthesis of divalent glycoamino acids with bis-triazole linkage

• Published in: Carbohydrate research Vol. 381; pp. 51 - 58
• Main Authors: Sahoo, Laxminarayan, Singhamahapatra, Anadi, Kumar, Keshav, Loganathan, Duraikkannu
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 15.11.2013; Elsevier
• Subjects: alkynes; Alkynes - chemistry; amino acids; Amino Acids - chemical synthesis; Amino Acids - chemistry; azides; Azides - chemistry; Biochemistry & Molecular Biology; Catalysis; Chemistry; Chemistry, Applied; Chemistry, Organic; Click reaction; copper; Copper - chemistry; Cyclization; Divalent glycoconjugates; Glycoamino acids; glycoconjugates; Glycopeptoid mimics; Life Sciences & Biomedicine; Molecular Structure; Physical Sciences; Science & Technology; Triazole; Triazoles - chemistry; Glycopeptoid mimics; Triazole; Click reaction; Divalent glycoconjugates; Glycoamino acids; PROTEIN
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2013.08.006

•Synthesis of bis triazole-linked divalent glycoconjugates.•Nitro- and cyano-functionalized dialkyne building blocks as precursors of α- and β-amino acids, respectively.•Triazole- and triazole amide-linked divalent glycoconjugates synthesized existed as rotamers. Triazole-linked diversely functionalized divalent glycoconjugates were synthesized using Cu(I) catalyzed [3+2] cycloaddition reaction of the desired azides and alkynes. A series of per-O-acetylated glycopyranosyl azides and per-O-acetylated glucopyranosyl azidoacetamide were reacted with nitro- and cyano-functionalized dialkyne building blocks as precursors of α- and β-amino acids, respectively. To introduce more conformational flexibility in the divalent molecules, peptoid-based triazole-linked divalent glycoconjugate was also synthesized.