2-deoxy-isoguanosines isoteric analogues and isoguanosine containing oligonucleotides
AssigneeBoehringer Mannheim GmbH
InventorsFrank Seela, Zigmunt Kasimierczuk, Klaus Muhlegger, Herbert Von Der Eltz
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Abstract
2'-Deoxyisoguanosine, isosteric analogues and isoguanosine derivatives of formulae I-V, processes for their production via compounds of the general formulae a or b and reaction with aroyl isocyanates or from compounds of the general formulae VI-IX by photochemical irradiation. A further production process is the conversion of deoxyguanosines or guanosines by means of persilylation, reaction with ammonia and deamination in the 2 position. The compounds are suitable as pharmaceutical agents with antiviral efficacy.
Claims4
An oligonucleotide capable of forming a parallel duplex structure, which comprises:
- ##STR1## wherein R.sub.3 is hydrogen or a protecting group, is hydrogen, halogen, a reporter group, an intercalator group, --NH(CH.sub.2).sub.n NH.sub.2 wherein n is a number from 2 to 12, or --R--CH.sub.2 COOH, wherein R is C.sub.1 -C.sub.8 alkylene.
A compound of formula:
- ##STR2## wherein R.sub.1 is a protecting group;
- R.sub.2 is a phosphoramidite or an H-phosphonate;
- R.sub.3 is hydrogen, or a protecting group, and
- Z is hydrogen, halogen, --NH(CH.sub.2).sub.n NH.sub.2 wherein n is a number from 2 to 12, or --R--CH.sub.2 COOH wherein R is C.sub.1 -C.sub.8 alkylene, a reporter group, or an intercalator group.
A process for making an oligonucleotide, comprising contacting a pre-existing oligonucleotide with a polymerase and a compound of formula:
- ##STR3## wherein R.sub.1 is P.sub.3 O.sub.9 H.sub.4, or an alpha, beta, or gamma thiophosphate of P.sub.3 O.sub.9 H.sub.4,
- R.sub.2 is hydroxy, a reporter group or an intercalator group,
- R.sub.3 is hydrogen or a protecting group,
- Z is halogen, --NH(CH.sub.2).sub.n NH.sub.2 wherein n is a number from 2 to 12, or --R--CH.sub.2 COOH, wherein R is C.sub.1 -C.sub.8 alkylene, a reporter group or an intercalator group, to incorporate said compound into said pre-existing oligonucleotide.
Dependencies are inferred from the claim text.