New 3'-derivatised oligo:nucleotide analogues

• Main Authors: UHLMANN, EUGEN., 61479 GLASHUETTEN, DE, CAROLUS, CAROLIN, 65321 FRANKFURT, DE, PEYMAN, ANUSCHIRWAN., 65779 KELKHEIM, DE
• Format: Patent
• Language: English; German
• Published: 21.12.1995
• Edition: 6
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; BEER; BIOCHEMISTRY; CHEMISTRY; COMPOSITIONS OR TEST PAPERS THEREFOR; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL ORENZYMOLOGICAL PROCESSES; DERIVATIVES THEREOF; ENZYMOLOGY; MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEICACIDS OR MICROORGANISMS; METALLURGY; MICROBIOLOGY; MUTATION OR GENETIC ENGINEERING; NUCLEIC ACIDS; NUCLEOSIDES; NUCLEOTIDES; ORGANIC CHEMISTRY; PROCESSES OF PREPARING SUCH COMPOSITIONS; SPIRITS; SUGARS; VINEGAR; WINE

3'-Modified oligonucleotides (I) and (II) and their salts are new. In the formula, Q = gp. (a), i.e. cpds. (I), or gp. (b), i.e. cpds. (II); a,b = 0-20; R = H; alkyl, alkenyl or alkynyl with up to 18C; 1-18C alkylcarbonyl; 2-19C alkenylcarbonyl; 3-19C alkynylcarbonyl; 6-20C aryl; 6-14C aryl-1-8C alkyl; or a gp. -P(W)(Z)(Z') (III); R = H; OH; 1-18C alkoxy; halo; N-3; or NH2; D = OH or OPO3<2->; B = conventional nucleotide base linked in the alpha- or beta-configuration; n = 1-100; n' = 0-50; m = 0-5; m' = 0-5 in cpds. (I) and 1-5 in cpds. (II); A = O; S or CH2; W = O, S or Se; V = O or sulphanediyl; T = O; sulphanediyl; NH; or CH2; X = OH or SH; U = OH; SH; BH3; SeH; alkyl or alkoxy with up to 18C; 6-20C aryl; 6-14C aryl-1-8C alkyl; NHR ; NR R ; or a gp. (OCH2CH2)pO(CH2)qCH2R (IV); R3 = 1-18C alkyl; 6-20C aryl; 6-14C aryl-1-8C alkyl; or (CH2)c-NH(CH2)cd-NR R ; and R = 1-18C alkyl; 6-20C aryl; or 6-10C aryl-1-8C alkyl; or NR R forms a 5- or 6-membered heterocycle opt. contg. O, S or additional N atom; c = 2-6; d = 0-6; p = 1-100; q = 0-22; R = H or functional gp., eg. OH, NH2, NHR , COOH, CONH2, COOR or halo; R = 1-6C alkyl; R = 1-4C alkyl; Z, Z' = OH; SH; SeH; 1-22C alkoxy; -O-(CH2)b-NR 'R '; 1-18C alkyl; 6-20C Ar ; 6-14C Ar -1-8C alkyl or alkoxy; 1-18C alkylmercapto; NHR ; NR R ; a gp. which promotes intracellular uptake or serves as a marker for a DNA probe or in the hybridisation of an oligonucleotide analogue to a target nucleic acid attaches by bonding, cross-linkage or cleavage; or a 5'- or 3'-linked nucleoside or oligonucleotide; b = 1-6; R ',R ' = as R and R ; or NR 'R ' forms a 3-6 membered ring; Ar = aryl or heteroaryl opt. mono-, di- or tri-substd. by COOH, NH2, NO2, 1-4C alkylamino, 1-6C alkoxy, OH, halo or CN; the brackets indicate that R and the adjacent phosphoryl gp. can be in the 2' and 3' positions or reversed in the 3' and 2' positions; and nucleotides present can have the D or L configuration.