- Novel chemoenzymatic protocol for the synthesis of 3′-O- dimethoxytrityl-2′-deoxynucleoside derivatives as building blocks for oligonucleotide synthesis
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An easy, efficient, and scalable chemoenzymatic strategy for the synthesis of 3′-O-dimethoxytrityl-2′-deoxynucleosides has been developed. A key feature of this approach is the regioselective synthesis of 5′-O-levulinyl-2′-deoxynucleosides through enzymatic acylation in the presence of Candida antarctica lipase B. In addition, it was observed that the deblocking of levulinyl group from the 5′-position is perfectly compatible with conventional base protecting groups. To demonstrate the scalability of this method, 3′-O-dimethoxytritylthymidine (4a) was synthesized on 25-g scale. These monomers (4a-d) are useful building blocks for the synthesis of oligonucleotides.
- Diaz-Rodriguez, Alba,Fernandez, Susana,Sanghvi, Yogesh S.,Ferrero, Miguel,Gotor, Vicente
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- Nucleosidyl-O-methylphosphonates: A pool of monomers for modified oligonucleotides
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An unique set of 5′-O- and 3′-O-phosphonomethyl derivatives of four natural 2′-deoxyribonucleosides, 1-(2-deoxy-β-D-threo- pentofuranosyl)thymine, 5′-O- and 2′-O-phosphonomethyl derivatives of 1-(3-deoxy-β-D-erythro-pentofuranosyl)thymine, and 1-(3-deoxy-β-D- threo-pentofuranosyl)thymine has been synthesized as a pool of monomers for the synthesis of modified oligonucleotides. The phosphonate moiety was protected with 4-methoxy-1-oxido-2-pyridylmethyl ester group, serving also as an intramolecular catalyst in the coupling step.
- Rejman, Dominik,Masojidkova, Milena,Rosenberg, Ivan
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p. 1683 - 1705
(2007/10/03)
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- Method for purifying protected 2'-deoxycytidines and hydrated crystals thereof
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A protected 2′-deoxycytidine is purified by precipitating the protected 2′-deoxycytidine represented by general formula (3) in the form of a hydrated crystal from a solution containing the protected 2′-deoxycytidine and water, and by recovering the protected 2′-deoxycytidine: wherein R1 represents a 4-methoxytrityl, 4,4′-dimethoxytrityl, or triphenylmethyl group; and B1 represents a cytosine group having a protected amino group. The compound represented by general formula (3) is, in particular, a protected 2′-deoxycytidine represented by formula (4): The 2′-deoxycytidine is used as a raw material for antisense DNA.
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- Synthesis of 3'-azido-3'-deoxythymidine-terminated oligonucleotide
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A method of completely chemical synthesis of 3'-azido-3'- deoxythymidine-terminated oligonucleotides via 5'-H-phosphonate of AZT is described.
- Esipov, Dmitriy S.,Esipova, Olga V.,Korobko, Vyacheslav G.
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p. 1697 - 1704
(2007/10/03)
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