First synthesis of alternating SATE-phosphotriester/ phosphodiester prooligonucleotides on solid support

• Published in: Bioorganic & medicinal chemistry letters Vol. 8; no. 20; pp. 2913 - 2918
• Main Authors: Tosquellas, Guilhem, Bologna, Jean Charles, Morvan, François, Rayner, Bernard, Imbach, Jean-Louis
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 20.10.1998; Elsevier
• Subjects: Animals; Carbohydrates. Nucleosides and nucleotides; Cell Extracts; Chemistry; Esterases - metabolism; Exact sciences and technology; Half-Life; Liver - enzymology; Liver - metabolism; Nucleosides, nucleotides and oligonucleotides; Oligonucleotides - chemical synthesis; Organic chemistry; Preparations and properties; Swine; Thymidine - chemistry; Automation; Nitrile; Enzyme; Organic phosphoramidite; Esterases; Organic thiophosphate; Hydrolysis resistance; Thioester; Analog; Hydrolases; Oligonucleotide; Solid phase; Oligodeoxyribonucleotide; Chemical synthesis; Pyrimidine nucleotide; Thymine nucleotide
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(98)00518-6

Prooligonucleotides with alternating S-Acyl-ThioEthyl (SATE) phosphotriester and phosphodiester linkages or a gap were synthesized by elimination of cyanoethyl group with non-nucleophilic base DBU. Their half-lives in the presence of Pig Liver Esterases (PLE) and in total cell extract were determined. Prooligonucleotides with an alternating SATE phosphotriester and phosphodiester or a gap were synthesized by elimination of cyanoethyl groups with non-nucleophilic base DBU in dry THF. Their half-lives in the presence of Pig Liver Esterases and in total cell extract were determined.