Thieme Chemistry Journals Awardees - Where Are They Now? Improved Fmoc Deprotection Methods for the Synthesis of Thioamide-Containing Peptides and Proteins.

Autor:	Szantai-Kis DM; Department of Biochemistry and Molecular Biophysics, Perelman School of Medicine, University of Pennsylvania, 3700 Hamilton Walk, Philadelphia, PA 19104, USA., Walters CR; Department of Chemistry, University of Pennsylvania, 231 S. 34 Street, Philadelphia, PA 19104, USA., Barrett TM; Department of Chemistry, University of Pennsylvania, 231 S. 34 Street, Philadelphia, PA 19104, USA., Hoang EM; Department of Chemistry, University of Pennsylvania, 231 S. 34 Street, Philadelphia, PA 19104, USA.; Swarthmore College, 500 College Ave, Swarthmore, PA 19081, USA., Petersson EJ; Department of Biochemistry and Molecular Biophysics, Perelman School of Medicine, University of Pennsylvania, 3700 Hamilton Walk, Philadelphia, PA 19104, USA.; Department of Chemistry, University of Pennsylvania, 231 S. 34 Street, Philadelphia, PA 19104, USA.
Jazyk:	angličtina
Zdroj:	Synlett : accounts and rapid communications in synthetic organic chemistry [Synlett] 2017 Sep; Vol. 28 (14), pp. 1789-1794. Date of Electronic Publication: 2017 Apr 10.
DOI:	10.1055/s-0036-1589027
Abstrakt:	Site-selective incorporation of thioamides into peptides and proteins provides a useful tool for a wide range of applications. Current incorporation methods suffer from low yields as well as epimerization. Here, we describe how the use of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) rather than piperidine in fluorenylmethyloxycarbonyl (Fmoc) deprotection reduces epimerization and increases yields of thioamide-containing peptides. Furthermore, we demonstrate that the use of DBU avoids byproduct formation when synthesizing peptides containing side-chain thioamides.
Databáze:	MEDLINE
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