Synthesis of divalent glycoamino acids with bis-triazole linkage.
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.
Department of Chemistry, Indian Institute of Technology Madras, Chennai 600036, India. Electronic address: laxminarayanchem@gmail.com.
Laxminarayan
L
Sahoo
Anadi
A
Singhamahapatra
Keshav
K
Kumar
Duraikkannu
D
Loganathan
D000480:Alkynes / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D014230:Triazoles / Q000737:chemistry*
D000480:Alkynes; D000596:Amino Acids; D001386:Azides; D014230:Triazoles; D003300:Copper
Click reaction; Divalent glycoconjugates; Glycoamino acids; Glycopeptoid mimics; Triazole