Synthesis of fish antifreeze neoglycopeptides using microwave-assisted "click chemistry"

Nicole Miller; Geoffrey M Williams; Margaret A Brimble

doi:10.1021/ol9005536

Synthesis of fish antifreeze neoglycopeptides using microwave-assisted "click chemistry"

Org Lett. 2009 Jun 4;11(11):2409-12. doi: 10.1021/ol9005536.

Authors

Nicole Miller¹, Geoffrey M Williams, Margaret A Brimble

Affiliation

¹ Department of Chemistry, University of Auckland, Private Bag 92019, Auckland, New Zealand.

PMID: 19473046
DOI: 10.1021/ol9005536

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemistry
Animals
Antifreeze Proteins / chemical synthesis*
Antifreeze Proteins / chemistry
Antifreeze Proteins / pharmacology*
Chemistry, Organic / methods*
Fishes / metabolism*
Glycopeptides / chemical synthesis*
Glycopeptides / chemistry
Glycopeptides / pharmacology*
Microwaves*
Peptides / chemical synthesis
Peptides / chemistry
Peptides / pharmacology*
Structure-Activity Relationship

Substances

Amino Acids
Antifreeze Proteins
Glycopeptides
Peptides