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1. (WO1998049183) BASE PROTECTING GROUPS AND PROCESS FOR OLIGONUCLEOTIDE SYNTHESIS

Pub. No.:    WO/1998/049183    International Application No.:    PCT/US1998/008901
Publication Date: Fri Nov 06 00:59:59 CET 1998 International Filing Date: Fri May 01 01:59:59 CEST 1998
IPC: C07H 21/00
Applicants: HYBRIDON, INC.
Inventors: AGRAWAL, Sudhir
IYER, Radhakrishnan, P.
HABUS, Ivan
YU, Dong
Title: BASE PROTECTING GROUPS AND PROCESS FOR OLIGONUCLEOTIDE SYNTHESIS
Abstract:
The invention provides new processes for synthesizing oligonucleotides that allow for deprotection of the oligonucleotide under more rapid and/or more mild conditions than existing methods. The invention further provides a nucleoside base protecting group of formula (I) that is stable under oligonucleotide synthesis conditions, but which can be removed under more mild conditions than existing protecting groups, as well as nucleoside synthons having such base protecting groups. The invention also provides oligonucleotides containing any of a variety of base labile functionalities and methods for using such oligonucleotides. In formula (I) wherein n1, n2 and n3 are independently 0-10, wherein a, b, c, d and e are each independently hydrogen, carbon or nitrogen, and wherein the ring structure bearing substituent R3 shown may be aromatic or heterocyclic, wherein the nitrogen displayed is the protected amino moiety of the nucleoside base, wherein R1, R2 and R3 are independently hydrogen, or an alkyl, aryl, aralkyl, ether, hydroxy, nitrile, nitro, ester, carboxyl, or aldehyde group, and wherein dotted lines represent alternative exocyclic or endocyclic double bonds; and removing the nucleoside base protecting group in ammonia gas.