000088464 001__ 88464
000088464 005__ 20180317093218.0
000088464 0247_ $$2doi$$a10.1002/chem.200501538
000088464 037__ $$aARTICLE
000088464 245__ $$aAryldithioethyloxycarbonyl (Ardec): A new family of amine protecting groups removable under mild reducing conditions and their applications to peptide synthesis
000088464 269__ $$a2006
000088464 260__ $$c2006
000088464 336__ $$aJournal Articles
000088464 520__ $$aThe development of phenyl-dithioethyloxycarbonyl (Phdec) and 2-pyridyldithioethyloxycarbonyl (Pydec) protecting groups, which are thiollabile 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 Nalpha-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-mercapto-ethanol and 1,8-diazobicyclo-[5.4.0]undec-7-ene (DBU) in N-methyl-pyrrolidinone for deprotection in an or ganic medium. Successful solid-phase synthesis of hexapeptides Ac-Lys-Asp-Glu-Val-Asp-Lys(Ardec)-NH 2 has clearly demonstrated the full orthogonality of these new amino protecting groups with Fmoc and Boc protections. The utility of the Ardec orthogonal deprotection strategy for site-specific chemical modification of peptides bearing several amino groups was illustrated firstly by the preparation of a fluorogenic substrate for caspase-3 protease containing the cyanine dyes Cy 3.0 and Cy 5.0 as FRET donor/acceptor pair, and by solid-phase synthesis of an hexapeptide bearing a single biotin reporter group. ©Wiley-VCH Verlag GmbH & Co. KGaA.
000088464 6531_ $$aEnzymes
000088464 6531_ $$aFluorescent probes
000088464 6531_ $$aFRET (fluorescence resonance energy transfer)
000088464 6531_ $$aPeptides
000088464 6531_ $$aProtecting groups
000088464 6531_ $$aSolid-phase synthesis
000088464 700__ $$aLapeyre, M.
000088464 700__ $$aLeprince, J.
000088464 700__ $$aMassonneau, M.
000088464 700__ $$aOulyadi, H.
000088464 700__ $$aRenard, P. Y.
000088464 700__ $$aRomieu, A.
000088464 700__ $$0240363$$aTurcatti, G.$$g103994
000088464 700__ $$aVaudry, H.
000088464 773__ $$j12$$k13$$q3655-3671$$tChemistry - A European Journal
000088464 909CO $$ooai:infoscience.tind.io:88464$$particle$$pSV
000088464 909C0 $$0252118$$pPTCB$$xU11378
000088464 937__ $$aEPFL-ARTICLE-88464
000088464 970__ $$a1/BSF
000088464 973__ $$aOTHER$$sPUBLISHED
000088464 980__ $$aARTICLE