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Alternative Procedures for the Synthesis of Methionine-Containing Peptide−Oligonucleotide Hybrids

2000; Wiley; Volume: 2000; Issue: 13 Linguagem: Inglês

10.1002/1099-0690(200007)2000

1434-193X

Vicente Marchán, Chryslaine Rodríguez‐Tanty, Marta Estrada, Enrique Pedroso, Anna Grandas,

DNA and Nucleic Acid Chemistry

European Journal of Organic ChemistryVolume 2000, Issue 13 p. 2495-2500 Full Paper Alternative Procedures for the Synthesis of Methionine-Containing Peptide−Oligonucleotide Hybrids Vicente Marchán, Vicente Marchán Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1−11, E-08028 Barcelona, Spain, Fax: (internat.) + 34-93/339-7878Search for more papers by this authorChryslaine Rodríguez-Tanty, Chryslaine Rodríguez-Tanty Present address: Centro Nacional de Investigaciones Científicas,Avenida 25 no. 15202, Playa 12100, Cubanacan, 6990 La Habana, CubaSearch for more papers by this authorMarta Estrada, Marta Estrada Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1−11, E-08028 Barcelona, Spain, Fax: (internat.) + 34-93/339-7878Search for more papers by this authorEnrique Pedroso, Enrique Pedroso Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1−11, E-08028 Barcelona, Spain, Fax: (internat.) + 34-93/339-7878Search for more papers by this authorAnna Grandas, Anna Grandas grandas@qo.ub.es Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1−11, E-08028 Barcelona, Spain, Fax: (internat.) + 34-93/339-7878Search for more papers by this author Vicente Marchán, Vicente Marchán Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1−11, E-08028 Barcelona, Spain, Fax: (internat.) + 34-93/339-7878Search for more papers by this authorChryslaine Rodríguez-Tanty, Chryslaine Rodríguez-Tanty Present address: Centro Nacional de Investigaciones Científicas,Avenida 25 no. 15202, Playa 12100, Cubanacan, 6990 La Habana, CubaSearch for more papers by this authorMarta Estrada, Marta Estrada Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1−11, E-08028 Barcelona, Spain, Fax: (internat.) + 34-93/339-7878Search for more papers by this authorEnrique Pedroso, Enrique Pedroso Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1−11, E-08028 Barcelona, Spain, Fax: (internat.) + 34-93/339-7878Search for more papers by this authorAnna Grandas, Anna Grandas grandas@qo.ub.es Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1−11, E-08028 Barcelona, Spain, Fax: (internat.) + 34-93/339-7878Search for more papers by this author First published: July 2000 https://doi.org/10.1002/1099-0690(200007)2000:13 3.0.CO;2-TCitations: 21AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Abstract The synthesis of methionine-containing peptide−oligonucleotide hybrids has been found to be best accomplished by a stepwise solid-phase approach in which peptide assembly using the sulfoxide derivative of methionine is followed by elongation of the oligonucleotide chain using the phosphite triester methodology, ammonia deprotection, and reduction of the sulfoxide to thioether by reaction with N-methylmercaptoacetamide. Quantitative amino acid incorporation yields could not always be achieved when the order of assembly of the two moieties was reversed, i.e. by elongating the peptide chain on a resin-linked oligonucleotide in order to avoid exposure of the thioether function to oxidizing conditions. Citing Literature Volume2000, Issue13July 2000Pages 2495-2500 RelatedInformation