Amidite for synthesizing modified nucleic acid and method...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C536S025340, C536S026800

Reexamination Certificate

active

07910726

ABSTRACT:
The disclosure provides an excellent amidite for synthesizing a modified nucleic acid, which enables a protective group therein to be removed under a moderate condition, thereby stably producing a hydroxyl group-containing modified nucleic acid. The disclosure also provides a method for synthesizing a modified nucleic acid using the amidite. Specifically, an amidite for synthesizing the modified nucleic acid is expressed by General Formula (I):where X represents a base, Y represents a substituent, Z represents a protective group for protecting a hydroxyl group in the substituent, and Q represents one of a hydrogen atom, a hydroxyl group and a hydroxyl group protected by a protective group, wherein the protective group can be removed in an aprotic solvent, and when the protective group is removed, the hydroxyl group emerges in the substituent.

REFERENCES:
patent: WO 03/078623 (2003-09-01), None
Kuijpers, W.H.A. et al; “The 2-(Acetoxymethyl) Benzoyl (AMB) Group As a New Base-Protecting Group, Designed for the Protection of (Phophate) Modified Oligonucleotides.”; Tetrahedron Letters, vol. 31, No. 46, pp. 6729-6732, 1990.
Eritja, Ramon et al; “A Synthetic Procedure for the Preparation of Oligonucleotides Without Using Ammonia and Its Application for the Synthesis of Oligonucleotides Containing O-4-Alkyl Thymidines.”; Tetrahedron, vol. 48, No. 20, pp. 4171-4182, 1992.
Avino, Anna Maria et al.; “Use of NPE-Protecting Groups for the Preparation of Oligonucleotides Without Using Nucleophiles During the Final Deprotection.”; Nucleosides & Nuceotides, vol. 13, No. 10, pp. 2059-2069, 1994.
Kuijpers, W.H.A. et al.; “The application of the AMB protective group in the solid-phase synthesis of methylphosphonate DNA analogues”; Nucleic Acids Research , vol. 21, No. 15, pp. 3493-3500, 1993.
Koole, Leo H. et al; “Synthesis of Phosphate-Methylated DNA Fragments Using 9-Fluorenylmethoxycarbonyl as Transient Base Protecting Group”; J. Org. Chem., vol. 54, pp. 1657-1664, 1989.
Heikkila, Jarmo et al.; “The 9- Fluorenylmethoxycarbonyl (Fmoc) Group for the Protection of Amino Functions of Cytidine, Adenosine, Guanosine and Their 2′-Deoxysugar Derivatives”; Acta Chemica Scandinavica., B37, No. 3, p. 263, 1983.

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