Patent ID: 6326358
Filing Date: 2001-12-04
Classification: C07H,C12N

Abstract:
A compound comprising a plurality of covalently-bound 2'-modified nucleosides having the formula: ##STR15##wherein:each B is a nucleobase;one of X.sub.1 or X.sub.2 is O, and the other of X.sub.1 or X.sub.2 is S;each R.sub.1, is, independently, hydroxyl, C.sub.1 -C.sub.20 alkyl, C.sub.3 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, halogen, thiol, keto, carboxyl, nitro, nitroso, nitrile, trifluoromethyl, trifluoromethoxy, O-alkyl, S-alkyl, NH-alkyl, N-dialkyl, O-aryl, S-aryl, NH-aryl, O-aralkyl, S-aralkyl, NH-aralkyl, amino, N-phthalimido, imidazole, azido, hydrazino, hydroxylamino, isocyanato, sulfoxide, sulfone, sulfide, disulfide, silyl, aryl, heterocycle, carbocycle, intercalator, reporter molecule, conjugate, polyamine, polyamide, polyalkylene glycol, or polyether;or R.sub.1 is a group of formula Z--R.sub.22 --(R.sub.23).sub.v ;Z is O, S, NH, or N--R.sub.22 --(R.sub.23).sub.v ;R.sub.22 is C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl, or C.sub.2 -C.sub.20 alkynyl;R.sub.23 is hydrogen, amino, halogen, hydroxyl, thiol, keto, carboxyl, nitro, nitroso, nitrile, trifluoromethyl, trifluoromethoxy, O-alkyl, S-alkyl, NH-alkyl, N-dialkyl, O-aryl, S-aryl, NH-aryl, O-aralkyl, S-aralkyl, NH-aralkyl, amino, N-phthalimido, imidazole, azido, hydrazino, hydroxylamino, isocyanato, sulfoxide, sulfone, sulfide, disulfide, silyl, aryl, heterocycle, carbocycle, intercalator, reporter molecule, conjugate, polyamine, polyamide, polyalkylene glycol, polyether;v is from 0 to about 10;or R.sub.1 has the formula: ##STR16##y1 is 0 or 1;y2 is independently 0 to 10;y3 is 1 to 10;E is C.sub.1 -C.sub.10 alkyl, N(Q.sub.1)(Q.sub.2) or N.dbd.C(Q.sub.1)(Q.sub.2);each Q.sub.1 and Q.sub.2 is, independently, H, C.sub.1 -C.sub.10 alkyl, substituted alkyl, dialkylaminoalkyl, a nitrogen protecting group, a tethered or untethered conjugate group, a linker to a solid support; or Q.sub.1 and Q.sub.2, together, are joined in a nitrogen protecting group or a ring structure that can include at least one additional heteroatom selected from N and O;or R.sub.1 has one of formula I or II: ##STR17##whereinZ.sub.0 is O, S, or NH;q.sup.1 is from 0 to 10;q.sup.2 is from 1 to 10;q.sup.3 is 0 or 1;q.sup.4 is, 0, 1 or 2;Z.sub.4 is OM.sub.1, SM.sub.1, or N(M.sub.1).sub.2 ;each M.sub.1 is, independently, H, C.sub.1 -C.sub.8 alkyl, C.sub.1 -C.sub.8 haloalkyl, C(.dbd.NH)N(H)M.sub.2, C(.dbd.O)N(H)M.sub.2 or OC(.dbd.O)N(H)M.sub.2 ;M.sub.2 is H or C.sub.1 -C.sub.8 alkyl;Z.sub.1, Z.sub.2 and Z.sub.3 comprise a ring system having from about 4 to about 7 carbon atoms, or having from about 3 to about 6 carbon atoms and 1 or 2 hetero atoms wherein said hetero atoms are selected from oxygen, nitrogen and sulfur, and wherein said ring system is aliphatic, unsaturated aliphatic, aromatic, or saturated or unsaturated heterocyclic; andZ.sub.5 is alkyl or haloalkyl having 1 to about 10 carbon atoms, alkenyl having 2 to about 10 carbon atoms, alkynyl having 2 to about 10 carbon atoms, aryl having 6 to about 14 carbon atoms, N(Q.sub.1)(Q.sub.2), OQ.sub.1, halo, SQ.sub.1 or CN;n is from 2 to 50; andm is 0 or 1.