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Nucleic Acids Research, 1987, Vol. 15, No. 4 1807-1818
© 1987

Articles

A model study directed towards the preparation of nucleopeptides via H-phosphonate intermediates

E. Kuyl-Yeheskiely, C.M. Tromp, A.H. Schaeffer, G.A. van der Marel and J.H. van Boom

Gorlaeus Laboratories PO Box 9502, 2300 RA Leiden, The Netherlands

Received December 3, 1986. Revised January 23, 1987. Accepted January 23, 1987.

The monofunctional phosphitylating reagents bis-(N,N-diethylamino)chloro-phoaphine and salicylchlorophosphine have been applied for the preparation of H-phosphonates of the amino acids serine, threonine and tyrosine. Experimental evidence showed that the latter reagent was less effective for the synthesis of a tyrosine H-phoshonate. The amino acids (peptide) H-phosphonates of serine or threonine proved to be suitable starting compounds for the formation of a phosphate diester bond with the 5'-OH of a d-nucleoside derivative using pivaloyl chloride as the activating reagent.


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