Aryldithioethyloxycarbonyl (Ardec): a new family of amine protecting groups removable under mild reducing conditions and their applications to peptide synthesis

Chemistry : a European Journal
Milaine LapeyreHubert Vaudry

Abstract

The development of phenyldithioethyloxycarbonyl (Phdec) and 2-pyridyldithioethyloxycarbonyl (Pydec) protecting groups, which are thiol-labile urethanes, is described. These new disulfide-based protecting groups were introduced onto the epsilon-amino group of L-lysine; the resulting amino acid derivatives were easily converted into N alpha-Fmoc building blocks suitable for both solid- and solution-phase peptide synthesis. Model dipeptide(Ardec)s were prepared by using classical peptide couplings followed by standard deprotection protocols. They were used to optimize the conditions for complete thiolytic removal of the Ardec groups both in aqueous and organic media. Phdec and Pydec were found to be cleaved within 15 to 30 min under mild reducing conditions: i) by treatment with dithiothreitol or beta-mercaptoethanol in Tris.HCl buffer (pH 8.5-9.0) for deprotection in water and ii) by treatment with beta-mercaptoethanol and 1,8-diazobicyclo[5.4.0]undec-7-ene (DBU) in N-methylpyrrolidinone for deprotection in an organic medium. Successful solid-phase synthesis of hexapeptides Ac-Lys-Asp-Glu-Val-Asp-Lys(Ardec)-NH2 has clearly demonstrated the full orthogonality of these new amino protecting groups with Fmoc and Boc protections. The ...Continue Reading

References

Oct 26, 1977·Journal of the American Chemical Society·G Barany, R B Merrifield
Nov 1, 1992·Journal of Biomolecular NMR·M PiottoV Sklenár
Mar 1, 1990·International Journal of Peptide and Protein Research·G B Fields, R L Noble
Apr 25, 1986·Nucleic Acids Research·P Marsh
Mar 1, 1993·Bioconjugate Chemistry·R B MujumdarA S Waggoner
Jan 1, 1997·Methods in Enzymology·I AnnisG Barany
Dec 1, 1999·Cell Death and Differentiation·H R Stennicke, G S Salvesen
Sep 9, 2000·Journal of Medicinal Chemistry·R V TalanianV L Cryns
Feb 13, 2001·Drug Discovery Today·M E. NuttallJ A. Erhardt
Oct 19, 2001·Genes and Immunity·A RichardsonD Kwiatkowski
Oct 24, 2001·The Journal of Organic Chemistry·Hugo E. GottliebAbraham Nudelman
Dec 26, 2001·Chemical Reviews·A MishraG B Behera
Dec 26, 2001·Chemical Reviews·D Kadereit, H Waldmann
Jul 5, 2002·Journal of Biomolecular Screening·Jarkko KarvinenIlkka Hemmilä
Jul 5, 2002·Journal of Biomolecular Screening·M PréaudatH Takemoto
Dec 12, 2002·Chemical Reviews·Jean-Bernard Denault, Guy S Salvesen
Dec 12, 2002·Journal of the American Chemical Society·Cleo M SalisburyJonathan A Ellman
Dec 19, 2002·Biophysical Chemistry·Mrudula Donepudi, Markus G Grütter
Feb 1, 2003·The Journal of Organic Chemistry·Aurélien Blanc, Christian G Bochet
Feb 18, 2003·Journal of Peptide Science : an Official Publication of the European Peptide Society·M MerglerT Vorherr
Mar 5, 2003·Bioorganic & Medicinal Chemistry·Carsten Schultz
Mar 20, 2003·Bioconjugate Chemistry·Niren MurthyPatrick S Stayton
Mar 20, 2003·Bioconjugate Chemistry·Christophe OlivierOleg Melnyk
Mar 20, 2003·Bioconjugate Chemistry·Line Bourel-BonnetOleg Melnyk
Jun 7, 2003·Organic Letters·Min LuTimothy M Dore
Jun 24, 2003·Bioorganic & Medicinal Chemistry·H Waldmann
Jul 23, 2003·Bioorganic & Medicinal Chemistry Letters·Eric DefrancqPascal Dumy
Sep 4, 2003·Journal of Peptide Science : an Official Publication of the European Peptide Society·M MerglerT Vorherr
Oct 3, 2003·Journal of Medicinal Chemistry·Norman KoglinAnnette G Beck-Sickinger
Mar 26, 2004·Organic Letters·Juan Jose Díaz-MochónMark Bradley
Jun 29, 2004·Angewandte Chemie·Marie-Priscille BrunChristiane Garbay
Jul 13, 2004·Trends in Biotechnology·Jean-Philippe Goddard, Jean-Louis Reymond
Nov 20, 2004·The Journal of Organic Chemistry·Abdallah HamzéJean-François Hernandez
Nov 20, 2004·The Journal of Organic Chemistry·Yashveer SinghPascal Dumy
Jan 7, 2005·Journal of Peptide Science : an Official Publication of the European Peptide Society·Thomas BerthelotLaurent Latxague
Mar 12, 2005·The Journal of Organic Chemistry·Ping Li, Barbara Ramsay Shaw
Mar 25, 2005·Organic Letters·Yashveer SinghPascal Dumy
Apr 1, 2005·Journal of Biomolecular Screening·Martha A O'BrienKeith V Wood

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Citations

Jun 14, 2014·European Journal of Medicinal Chemistry·Alfonso LatorreÁlvaro Somoza
Apr 9, 2015·Journal of Peptide Science : an Official Publication of the European Peptide Society·Chenhong WangNing Zhou
Jun 6, 2014·Chemical Communications : Chem Comm·Taeyoung KimJong Seung Kim
Feb 10, 2010·Chemistry : a European Journal·Ludivine Louise-LerichePierre-Yves Renard
Oct 6, 2010·Chemical Communications : Chem Comm·Dmitri A OssipovJöns Hilborn
Jun 18, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Florian GauthierFrançoise Debart
Apr 15, 2009·Chemical Reviews·Albert Isidro-LlobetFernando Albericio
Aug 10, 2011·Tetrahedron Letters·Joshua D Thomas, Terrence R Burke

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