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REGIO- AND STEREOSPECIFIC SYNTHESIS OF 7-DEAZAPURINE 2'-DEOXYRIBONUCLEOSIDES AND INCORPORATION OF NUCLEOSIDE ISOSTERES INTO OLIGONUCLEOTIDES
Seela, F. Driller, H. Kehne, A. Menkhoff, S. Ott, J. Winkeler, H.-D.
Seela, F.
Driller, H.
Kehne, A.
Menkhoff, S.
Ott, J.
Winkeler, H.-D.
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Issue Date
1987
Submitted date
2023-04-19
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Abstract
2'-Deoxytubercidin and 7-deaza-2'-deoxyguanosine, isosteres of the parent nucleosides 2'-deoxyadenosine and 2'-deoxyguanosine have been synthesized via phase-transfer glycosylation of appropriately protected pyrrolo[2,3-d]pyrimidines with 1-chloro-2-deoxy-3 ,5-di-O-p-toluoy1-Derythro- pentofuranose via a regio- and stereospecific route. The nuclecside isosteres were provided with suitable protecting groups and converted into their O-3'-phosphoramidites. Application of these compounds in solid-support oligonucleotide synthesis yielded self-complementary oligomers with alternating d(TuT) or d(c’Gc) sequences. Additionally the incorporation of the 7-deazapurine 2'-deoxyribofuranosides into the Eco RI sequence was accomplished. Applying phosphite triester condensation in solution, (2',5')- and (3',5')-tubercidylyl-tubercidins were synthesized.
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Chemical synthesis in molecular biology, 29 ff
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conference paper
conference paper
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en
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GBF Monographs, Vol. 8
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0930-4320
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Attribution-NonCommercial-ShareAlike 4.0 International