Synthesis of glycopolypeptides by the ring opening polymerization of O-glycosylated-α-amino acid N-carboxyanhydride (NCA)

D Pati, AY Shaikh, S Hotha, SS Gupta - Polymer Chemistry, 2011 - pubs.rsc.org
Polymer Chemistry, 2011pubs.rsc.org
The novel synthesis of O-glycosylated lysine-NCA from a stable glycosyl donor and a
commercially available protected amino acid in very high yield is reported. These O-
glycosylated lysine-NCA monomers underwent ring opening polymerization using simple
primary amine initiators to form well defined, high molecular weight homoglycopolypeptides
and diblock co-glycopolypeptides. The synthesis of azide labelled end functionalized
glycopolypeptides and amphiphilic diblock copolypeptides is also reported. This …
The novel synthesis of O-glycosylated lysine-NCA from a stable glycosyl donor and a commercially available protected amino acid in very high yield is reported. These O-glycosylated lysine-NCA monomers underwent ring opening polymerization using simple primary amine initiators to form well defined, high molecular weight homoglycopolypeptides and diblock co-glycopolypeptides. The synthesis of azide labelled end functionalized glycopolypeptides and amphiphilic diblock copolypeptides is also reported. This methodology represents an easy and practical route to the synthesis of O-glycosylated polypeptides with 100% glycosylation.
The Royal Society of Chemistry
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