The P-Stereocontrolled Synthesis of PO/PS-Chimeric Oligonucleotides by Incorporation of Dinucleoside Phosphorothioates Bearing anO-4-Nitrophenyl Phosphorothioate Protecting Group

Autor:	Geneviève Pratviel, Bernard Meunier, Lucyna A. Wozniak, Wojciech J. Stec, Malgorzata Bukowiecka-Matusiak, Marcin Góra, Sophie Mourgues
Rok vydání:	2005
Předmět:	Exonuclease biology Chemistry Oligonucleotide Stereochemistry Organic Chemistry Absolute configuration Diastereomer Stereospecificity Human plasma biology.protein 4-nitrophenyl phosphorothioate Physical and Theoretical Chemistry Protecting group
Zdroj:	European Journal of Organic Chemistry. 2005:2924-2930
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.200400910
Popis:	The synthesis of protected model dinucleoside (3',5')-O-aryl phosphorothioates, their separation into pure diastereomers, and their successful incorporation into oligonucleotides followed by stereospecific deprotection of the O-aryl phosphorothioate function with oximate ion (inversion) enables the preparation of chimeric PO/PS-oligonucleotides with a predetermined sense of P-chirality at each internucleotide phosphorothioate position. The absolute configuration at the phosphorus of the internucleotide O-aryl phosphorothioate in “dimeric building blocks” has been assigned. The 3'-terminal SP-phosphorothioate linkages effectively protect such chimeric constructs from degradation by human plasma exonuclease (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
Databáze:	OpenAIRE
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