Synthesis of oligonucleotides on cellulose by a phosphotriester method (original) (raw)
Journal Article
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Department of Organic Chemistry
Genentech, Inc., 460 Point San Bruno Blvd., South San Francisco, CA 94080, USA
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Department of Organic Chemistry
Genentech, Inc., 460 Point San Bruno Blvd., South San Francisco, CA 94080, USA
Search for other works by this author on:
Received:
22 January 1980
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Abstract
The synthesis of oligothymidilic acids, (dT) m (where m = 4, 7, 10, 13, 16, 19, 22, and 25), was carried out using a solid phase approach in combination with the modified phosphotriester methodology developed in solution. Cellulose was used as the solid support after its functionalization with a specially featured dinucleoside diphosphate, 5′-O-p-chlorophenylphospho-2′(3′)-0-acetyluridilyl-[2′(3′)-3′]-5′-0-dimethoxytritylthymidine p-chloro-phenylester. The fully protected trideoxynucleoside triphosphste containing only thymidine was repeatedly used to elongate the oligonucleotide chain in the 3′-5′ direction. Individual coupling yields ranged from 45% to 75%. The total time needed to prepare (dT) 25 was four days. Similarly, the tridecanucleotide d(AGAAGGTACTTTT) was synthesized in good yield. The results show that this approach can be used for a fast and economic way to synthesize oligodeoxynucleotides.
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© 1980 IRL Press Limited
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