Abstract
Over the last 30 years or so, the chemical synthesis of deoxyribonucleic acid (DNA) and ribonucleic acid (RNA) has constituted one of the most challenging problems in the field of the synthetic organic chemistry of natural products. In more recent times, attention has been focused not on “natural” nucleic acid fragments, but on the preparation of nucleic acids bearing modified internucleotidic linkages or modified bases in an effort to enhance stability to nucleases and increase cellular uptake.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Reese, C. B. (1978) Tetrahedron 34, 3143.
For other general reviews on the chemical synthesis of DNA, see refs. 4 and 5; Sonveaux, E. (1986) Bioorg. Chem. 14, 274–325; English, U. and Gauss, D. H. (1991) Augew. Chem. Int. Ed. Engl. 30,613–722; Uhlmann, E. and Peyman, A. (1990) Chem. Rev. 90, 544–584; Davies, J. E. and Gassen, H. G. (1983) Angew. Chem. Int. Ed. Engl. 22, 13–31.
Gait, M. J., Singh, M., Sheppard, R. C, Edge, M. D., Greene, A. R., Heathcliffe, G. R., Atkinson, T. C, Newton, C. R., and Markham, A. F. (1980) Nucl. Acids Res. 8, 1081–1096.
Gait, M. J., Matthes, H. W. D., Singh, M., Sproat, B. S., and Titmas, R. C. (1982) Nucleic Acids Res. 10, 6243–6254.
Gait, M. J. (ed.) (1984) Oligonucleotide Synthesis. A Practical Approach. IRL Press, Oxford Chapter 4.
For a review, see Caruthers, M. H. (1991) Acc. Chem. Res. 24, 278–284.
Gough, G. R., Brunden, M. J., and Gilham, P. T. (1981) Tetrahedron Lett. 22, 4177–4180.
Koster, H., Stumpe, A., and Wolter, A. (1983) Tetrahedron Lett. 24, 747–750.
Sproat, B. S. and Bannwarth, W. (1983) Tetrahedron Lett. 24, 5771–5774.
Atherton, E., Brown, E., Sheppard, R. C, and Rosevear, A. (1981) J. Chem. Soc. Commun., 1151–1152.
Chattopadhyaya, J. B. and Reese, C. B. (1978) J. Chem. Soc. Commun. 639–640.
Schaller, H., Weimann, B., Lerch, B., and Khorana, H. G. (1963)7. Am. Chem. Soc. 85, 3821–3827.
Reese, C. B. (1970) Colloques International du C.N.R.S. 182, 319–328.
Reese, C. B., Titmas, R. C, and Yau, L. (1978) Tetrahedron Lett. 30, 2727–2730.
Reese, C. B. and Zard, L. (1981) Nucl. Acids Res. 9, 4611–4626.
Khorana, H. G. (1968) Pure Appl. Chem. 17, 349–381.
Agarwal, K. L., Yamazaki, A., Cashion, P. J., and Khorana, H. G. (1972) Angew. Chem. Int. Ed. Engl. 11, 451–459.
Kuwe, A., Sekine, M., and Hata, T. (1982) Tetrahedron Lett. 23, 4365–4368.
Kuwe, A., Sekine, M., and Hata, T. (1983) Chem. Lett. 1597–1600.
Froehler, B. C. and Matteucci, M. D. (1983) Nucl. Acids Res. 11, 8031–8036.
Cohen, A. S., Najaman, D. R., Paulus, A., Guttman, A., Smith, J. A., and Karger, B. L. (1988) Proc. Natl. Acad. Sci. USA 85, 9660–9663.
Guttman, A., Cohen, A. S., Heiger, D. N., and Karger, B. L. (1990) Anal. Chem. 62, 137–141.
Efimov, U. A., Reverdatto, S. V., and Chakhmakhcheva, O. G. (1982) Nucl. Acids Res. 10, 6675–6694.
Ejimov, V. A., Chakhmakhcheva, O. G., and Ovchinnikov, Y. A. (1985) Nucl. Acids Res. 13, 3651–3666.
Froehler, B. C. and Matteucci, M. D. (1985) J. Am. Chem. Soc. 107, 278–279.
Sproat, B. S., Rider, P., and Beijer, B. (1986) Nucl. Acids Res. 14, 1811–1824.
Efimov, V. A., Burgakova, A. A., Dubey, I. Y., Polushin, N. N., Chakhmakhcheva, O. G., and Orchinnikov, Y. A. (1986) Nucl. Acids Res. 14, 6525–6540.
Reese, C. B. and Ubasawa, A. (1980) Tetrahedron Lett. 21, 2265–2268.
Kamimura, T., Tsuchiya, M, Koura, K., Sekine, M, and Hata, T. (1983) Tetrahedron Lett. 24, 2775–2778.
Trichtinger, T., Charubala, R., and Pfleiderer, W. (1983) Tetrahedron Lett. 24, 711–714.
Jones, S. S., Reese, C. B., Sibanda, S., and Ubasawa, A. (1981) Tetrahedron Lett. 22, 4755–4758.
Reese, C. B. and Skone, P. A. (1984) J. Chem. Soc. Perkin Trans. 1, 1263–1271.
Boom, J. H. van, Burgers, P. M. J., Deursen, P. H. van, Rooy, J. F. M., and Reese, C. B. (1976)7. Chem. Soc. Chem. Commun. 167, 168.
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1993 Humana Press Inc., Totowa, NJ
About this protocol
Cite this protocol
Christodoulou, C. (1993). Oligonucleotide Synthesis. In: Agrawal, S. (eds) Protocols for Oligonucleotides and Analogs. Methods in Molecular Biology, vol 20. Humana Press. https://doi.org/10.1385/0-89603-281-7:19
Download citation
DOI: https://doi.org/10.1385/0-89603-281-7:19
Publisher Name: Humana Press
Print ISBN: 978-0-89603-281-1
Online ISBN: 978-1-59259-507-5
eBook Packages: Springer Protocols