Nucleoside derivatives with photo-unstable protective groups

Details Nucleoside derivatives with photo-unstable protective groups Nucleoside derivatives with photo-unstable protective groups

2002-02-21

2004-06-29

Riley, Jezia (Department: 1637)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C536S024300, C536S025300, C536S026600

Reexamination Certificate

active

06756492

ABSTRACT:

FIELD OF THE INVENTION
The subject matter of the present invention relates to nucleoside derivatives with photolabile protective groups, a method for the production thereof, their use and nucleic acid chips built up therefrom.
BACKGROUND OF THE INVENTION
Photolabile protective groups are of significance for the hydroxy and phosphate functions in nucleosides and/or nucleotides since they are suitable for the light-controlled parallel synthesis of oligonucleotides on a solid support surface (Fodor et al., Science 1991, 251, p. 767 et seq.). It is possible to synthesize therewith oligonucleotides or nucleic acid chips which can be used for sequencing nucleic acids efficiently, for example.
To date, it is only known to produce DNA chips by means of photolithographic methods using 3′-O phosphite amides, which correspondingly carry the temporary photolabile protective group at the 5′-O position (WO-A-96/18634). It is possible to produce DNA chips by means of these nucleic acid building blocks, the oligomer being built up from the 3′ end to the 5′ end. The finished oligomer is thus anchored to the solid phase via the 3′-O end. The 5′-OH end can be accessed freely. DNA chips which were produced with this method can be used for hybridization experiments but not for certain enzyme reactions (e.g. with DNA polymerase or ligase) which require free 3′-OH.
SUMMARY OF THE INVENTION
It is the object of this invention to provide 3′-photolabile nucleosides and their derivatives and to generate nucleic acid chips using the 3′-photolabile nucleosides obtained therefrom, in which the oligomers built up by light-controlled synthesis are linked to the solid phase via the 5′ end and thus enable enzyme reactions at the 3′ end.


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