Synthesis of prenylated peptides and peptide esters

Biopolymers
F R Naider, J M Becker

Abstract

Modification of the cysteine sulfur in peptides and proteins to a thioether is a recently described posttranslational event that results in the incorporation of farnesyl and geranylgeranyl moieties. The increased lipophilicity accompanying these modifications often causes localization of the resulting protein to the membrane and may be essential for biological activity. Methods are described to chemically and biochemically synthesize farnesylated and geranylgeranylated peptides and proteins from microgram to gram quantities. Conditions for thioalkylation include acidic, neutral, and basic media. The ability to readily form peptidylthioethers will greatly facilitate studies of biologically important proteins and peptides containing isoprenyl moieties.

References

Jan 1, 1992·Annual Review of Biochemistry·J Kurjan
Dec 1, 1992·Biochemistry·Y T MaR R Rando
May 15, 1992·Proceedings of the National Academy of Sciences of the United States of America·M N AshbyJ Rine
Oct 1, 1990·International Journal of Peptide and Protein Research·C B XueF Naider
Jul 14, 1989·Biochemical and Biophysical Research Communications·C B XueF Naider
Jan 1, 1995·Methods in Enzymology·J A ThissenP J Casey
Jan 1, 1995·Methods in Enzymology·B A GilbertR R Rando
Jan 1, 1995·Methods in Enzymology·M N Ashby, J Rine
Jan 1, 1995·Methods in Enzymology·P B CassidyC D Poulter
May 23, 1995·Proceedings of the National Academy of Sciences of the United States of America·J M Dolence, C D Poulter
Feb 3, 1995·Journal of Medicinal Chemistry·D V PatelL Hunihan
Mar 21, 1995·Biochemistry·C SherrillD Roise
May 1, 1994·Analytical Biochemistry·N H GeorgopapadakouJ D Watkins
Jan 19, 1996·Journal of Medicinal Chemistry·J T HuntV Manne
Mar 8, 1996·The Journal of Biological Chemistry·P J Casey, M C Seabra
May 1, 1996·International Journal of Peptide and Protein Research·G Byk, D Scherman
Oct 1, 1996·International Journal of Peptide and Protein Research·M KoppitzH Kessler

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Citations

Mar 27, 2009·The Journal of Organic Chemistry·James L DonelsonRichard A Gibbs
May 12, 2009·Journal of the American Chemical Society·James W WollackMark D Distefano
Jan 21, 2016·Journal of Peptide Science : an Official Publication of the European Peptide Society·Raymond BehrendtJohn Offer
Oct 13, 2006·Angewandte Chemie·Luc BrunsveldHerbert Waldmann
Jan 20, 2006·Journal of Mass Spectrometry : JMS·Michael D Hoffman, Juergen Kast
Dec 17, 2008·Angewandte Chemie·Christian P R Hackenberger, Dirk Schwarzer
Apr 20, 2010·Journal of Peptide Science : an Official Publication of the European Peptide Society·Daniel G MullenMark D Distefano
Oct 3, 2006·Methods : a Companion to Methods in Enzymology·L BrunsveldH Waldmann
Nov 3, 2015·Organic Letters·Enrica CalceStefania De Luca
Sep 27, 2005·Bioorganic & Medicinal Chemistry Letters·Brian S HenriksenRichard A Gibbs
Aug 20, 2016·Chemistry : a European Journal·Enrica Calce, Stefania De Luca
Jan 5, 2002·Biopolymers·J P TamK D Eom
Feb 24, 2000·Biopolymers·J P TamZ Miao
Apr 22, 2014·Amino Acids·Enrica CalceStefania De Luca
Jun 23, 2000·The Journal of Peptide Research : Official Journal of the American Peptide Society·H XieF Naider
Jan 29, 2021·Chembiochem : a European Journal of Chemical Biology·Aline D de AraujoDavid P Fairlie

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