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Nucleic Acids Research, 1985, Vol. 13, No. 12 4485-4502
© 1985

Articles

Chemical synthesis of oligonucleotides containing a free sulphydryl group and subsequent attachment of thiol specific probes

Bernard A. Connolly* and Peter Rider

Department of Biochemistry, University of Southampton Bassett Crescent East, Southampton SO9 3TU, UK European Molecular Biology Laboratory Meyerhofstr. 1, 6900 Heidelberg, FRG

*To whom correspondence should be addressed

Received April 22, 1985. Accepted May 22, 1985.

Oligonucleotides containing a free sulphydryl group at their 5'-termini have been synthesised and further derivatised with thiol specific probes. The nucleotide sequence required is prepared using standard solid phase phosphor-amidlte techniques and an extra round of synthesis is then performed using the S-triphenylmethyl O-methoxymorpholinophosphite derivatives of 2-mercap-toethanol, 3-mercaptopropan (l)ol or 6-mercaptohexan(l)ol. After cleavage from the resin and removal of the phosphate and base protecting groups, this yields an oligonucleotide containing an S-triphenylmethyl group attached to the 5'-phosphate group via a two, three or six carbon chain. The triphenyl-methyl group can be readily removed with silver nitrate to give the free thiol. With the three and six carbon chain oligonucleotides, this thiol can be used, at pH 8, for the attachment of thiol specific probes as illustrated by the reaction with fluorescent conjugates of iodoacetates and maleiimides. However, oligonucleotides containing a thiol attached to the 5'-phosphate group via a two carbon chain are unstable at pH 8 decomposing to the free 5'-phosphate and so are unsuitable for further derivatisation


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