2'-deoxy-3'-phosphonylmethyl nucleosides

Details 2'-deoxy-3'-phosphonylmethyl nucleosides 2'-deoxy-3'-phosphonylmethyl nucleosides

C - Chemistry, Metallurgy

07

H

195/139, 260/229

C07H 19/04 (2006.01) C07H 19/10 (2006.01) C07H 19/20 (2006.01) C12P 19/38 (2006.01)

Patent

CA 1254887

ABSTRACT The invention relates to 2'deoxy-3'-phosphonylmethyl nucleosides that are not substituted in the 2'-position, of the following general formula Image in which the following symbols have the following meanings: B = adenine, N6-benzoyladenine; guanine, N2-isobutyryl guanine, N2-isobutyryl-4-0- (p-nitrophenyl ethyl)-guanine; cytosine, N4-benzoyl cytosine, 4-anisoyl cytosine; thymine, 4-0-(p-nitrophenylethyl)-thymine; or uracil, and (a) X1, X2 = H, alkali. metal, NH4 or C1-4-alkyl; or X1 = chlorophenyl, 2,2,2-trichloroethyl or cyanoethyl and X2 = triethylammonium and R = OH, N3, NH2, NHR1, NR1R2, -O-PO(OY1)(OY2), -O-PS(OY1)(OY2), -O-PO(OY1-O-PO(OY2)(OY3), -O-PO(OY1)-O-PO(OY2)-O-PO(OY3)(OY4) R1, R2 = C1-4-alkyl, C4-7-cycloalkyl, C6-8-alkylaryl or C6-8-arylalkyl, and Y1, Y2, Y3, Y4 = H, alkali metal or NH4, or R = 5'-O-monomethoxytriphenylmethyl (S'-O-monomethoxy- trityl) or 5'-0-(4,4'-dimethoxytriphenylmethyl) (5'-0- (4,4'-dimethoxytrityl)) or (b) X1 = H, alkali metal, NH4 or C1-4-alkyl, X and R being absent with the formation of a ring of the grouping -PO(OX1)-O-CH2-. The novel nucleosides when incorporated into DNA, result in nucleotide sequences which cannot be cleaved by nucleases.

448788

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