Synthesis of fish antifreeze neoglycopeptides using microwave-assisted "click chemistry".
Microwave-enhanced click glycoconjugation of a propargylated alpha-GalNAc sugar moiety with an azido-functionalized amino acid or multiazido-functionalized peptides using a catalytic quantity of Cu(I) enabled a high-yielding and rapid synthesis of a "Tn-antigen mimic" and click analogues of antifreeze glycopeptides, thus demonstrating a valuable synthetic platform for the synthesis of biologically relevant neoglycopeptides.
Miller
Nicole
N
Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand.
Williams
Geoffrey M
GM
Brimble
Margaret A
MA
D000596:Amino Acids / Q000737:chemistry; D000818:Animals; D021301:Antifreeze Proteins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002625:Chemistry, Organic / Q000379:methods*; D005399:Fishes / Q000378:metabolism*; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008872:Microwaves; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000596:Amino Acids; D021301:Antifreeze Proteins; D006020:Glycopeptides; D010455:Peptides