Method for preparing 3′-O-amino-2′-deoxyribonucleoside-5′-triphosphate
AssigneesDNA Script, Institut Pasteur, Centre National De La Recherche Scientifique
InventorsIvo Sarac, Marcel Hollenstein
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Abstract
The invention relates to a method for preparing 3′-O-amino-2′-deoxyribonucleoside-5′-triphosphate. It also relates to a solid support functionalized with at least one N-hydroxyphthalimide moiety and uses thereof for protecting 3′-hydroxy group of a 2′-deoxyribonucleoside during synthesis of a nucleoside or a derivative thereof.
Claims13
A method for preparing 3′-O-amino-2′-deoxyribonucleoside-5′-triphosphate, said method comprising the steps of:
- (a) protecting 5′-hydroxy group of a 2′-deoxyribonucleoside;
- (b) converting (S)-3′-hydroxy group of the compound obtained in step (a) into (R)-3′-hydroxy group;
- (c) grafting the compound obtained in step (b) on a solid support functionalized with at least one N-hydroxyphthalimide moiety, wherein said at least one N-hydroxyphthalimide moiety is represented by formula (I):
- wherein L represents a linker, under conditions allowing (R)-3′-hydroxy group of the compound obtained in step (b) to be substituted by a N-hydroxyphthalimide moiety of the functionalized solid support;
- (d) deprotecting 5′-hydroxy group of the compound obtained in step (c);
- (e) triphosphorylating 5′-hydroxy group of the compound obtained in step (d);
- (f) reacting the compound obtained in step (e) with a cleaving reagent selected from the group consisting of primary amines, hydrazine and hydroxides;
- and,
- (g) optionally recovering 3′-O-amino-2′-deoxyribonucleoside-5′-triphosphate obtained in step (f).
A 3′-O-amino-2′-deoxyribonucleoside-5′-triphosphate grafted on a solid support functionalized with at least one N-hydroxyphthalimide moiety, wherein said at least one N-hydroxyphthalimide moiety is represented by formula (I):
- wherein L represents a linker.
Dependencies are inferred from the claim text.