O-Glycosylation of Unprotected Peptides

Hisashi Yamamoto; Takahiro Sawano

doi:10.1055/s-0037-1612282

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Synfacts 2019; 15(04): 0445
DOI: 10.1055/s-0037-1612282

Peptide Chemistry

O-Glycosylation of Unprotected Peptides

Contributor(s):

Hisashi Yamamoto

,

Takahiro Sawano

Wadzinski TJ, Steinauer A, Hie L, Pelletier G, Schepartz A. * Miller SJ. * Yale University, New Haven, USA
Rapid Phenolic O-Glycosylation of Small Molecules and Complex Unprotected Peptides in Aqueous Solvent.

Nat. Chem. 2018;
10: 644-652

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Further Information

Publication History

Publication Date:
19 March 2019 (online)

Abstract
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Key words

glycosylation - fluoroglycosides - calcium hydroxide

Significance

A number of glycosylated natural products and synthetic glycopeptides can be found in important biochemical probes and therapeutic agents. The authors have developed an efficient phenolic O-glycosylation of small molecules, unprotected tyrosine, and complex unprotected peptides in aqueous solvent.

Comment

The glycosylation, employing glycosyl fluoride donors and Ca(OH)₂, proceeds rapidly at room temperature to give high yields of the glycosylated products.

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