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Nucleic Acids Research, 1987, Vol. 15, No. 17 6991-7004
© 1987

Articles

Synthesis and resistance to enzymic hydrolysis of stereochemically-defined phosphonate and thiophosphate analogues of P1, P4-bis(5'-adenosyl) tetraphosphate

G.M. Blackbum, G.E. Taylor, G.R.J. Thatcher, M. Prescott1 and A.G. McLennan1

Department of Chemistry, University of Sheffield Sheffield S3 7HF 1Department of Biochemistry, University of Liverpool Liverpool L69 3BX, UK

Received July 2, 1987. Revised August 12, 1987. Accepted August 12, 1987.

Novel analogues of P1, P4-bis(5'adenosyl) tetraphosphate, Ap4A (1), have been prepared with sulphur substituents at P1 and P4 and either oxygen or methylene bridges at the P2, P3-position. Separation of three isomers of the ApspCH2pps A species has been achieved by a combination of mplc and hplc and the Rp, Rp, Rp,Sp, and Sp,Sp diastereoisomers identified on the basis of selective enzymatic hydrolysis using snake venom phosphodiesterase. Each of these three isomers is a strong competitive inhibitor of the specific Ap4Aase from Artemia and is highly resistant to the asymmetric cleavage normally catalysed by this enzyme.


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