Synthesis and properties of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl oligonucleotides

Cicero, Daniel O.; Gallo, Mariana; Neuner, Philippe; Iribarren, Adolfo M.

doi:10.1016/s0040-4020(01)00745-1

Cited by 10 publications

(13 citation statements)

References 20 publications

(35 reference statements)

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“…As expected, the binding affinity of the 2'-methyl down oligomers for complementary DNA and RNA was reduced in comparison with unmodified sequences, or even no cooperative melting was observed. On the other hand, 2'-methyl up oligonucleotides exhibited a thermal stability that depended on the sequence and the length of the modified oligonucleotide (17,18). The reason why the (2'S)-methyloligodeoxynucleotides hybridize better than the (2'R) analogs could be attributed to the fact that the first ones have the right preorganization to fit the complementary RNA strand (19), since the sugar moieties are locked in the 3'-endo conformation.…”

Section: Sugar Modificationsmentioning

confidence: 99%

Design and applications of modified oligonucleotides

Gallo

Montserrat

Iribarren

2003

Braz J Med Biol Res

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Oligonucleotides have a wide range of applications in fields such as biotechnology, molecular biology, diagnosis and therapy. However, the spectrum of uses can be broadened by introducing chemical modifications into their structures. The most prolific field in the search for new oligonucleotide analogs is the antisense strategy, where chemical modifications confer appropriate characteristics such as hybridization, resistance to nucleases, cellular uptake, selectivity and, basically, good pharmacokinetic and pharmacodynamic properties. Combinatorial technology is another research area where oligonucleotides and their analogs are extensively employed. Aptamers, new catalytic ribozymes and deoxyribozymes are RNA or DNA molecules individualized from a randomly synthesized library on the basis of a particular property. They are identified by repeated cycles of selection and amplification, using PCR technologies. Modified nucleotides can be introduced either during the amplification procedure or after selection.

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Section: Sugar Modificationsmentioning

confidence: 99%

Design and applications of modified oligonucleotides

Gallo

Montserrat

Iribarren

2003

Braz J Med Biol Res

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“…s, HNCO). 13 C-NMR (CDCl 3 ): 11.2 (MeÀC(2')); 12.5, 12.9, 13.5 (Me 2 CH); 16.9 ± 17.4 (Me 2 CH); 44.8 (C(2')); 60.6 (C(5')); 73.3 (C(3')); 84.4 (C(4')); 86.1 (C(1')); 122.9 (C(5)); 128.1 (C o ); 129.8 (C m ); 131.8 (C p ); 133.9 (C ipso ); 141.6 (C(8)); 149.8 2 ) (C(4)); 151.4 2 ) (C(6)); 152.3 (C (2) (2'S)-N 6 -Benzoyl-2'-deoxy-2'-C-methyladenosine (11). A soln.…”

Section: Experimental Partmentioning

confidence: 99%

“…calc. for C 11 (2'S)-2'-Deoxy-6-O-(2,6-dichlorophenyl)-2'-C-methylinosine (13). Compound 8a (569 mg, 0.87 mmol) was desilylated as described above for 11.…”

Section: Experimental Partmentioning

confidence: 99%

“…calc. for C 11 (2'S)-N 6 -Benzoyl-2'deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-C-methyladenosine (15). Compound 11 (86 mg, 0.23 mmol) was dried by evaporation of pyridine.…”

Section: Experimental Partmentioning

confidence: 99%

“…For example, 2'-O-alkyloligoribonucleotides [7] [8] show increased nuclease resistance and form stable duplexes and 2'-O-methoxyethyloligonucleotides [9] seem to be very promising. The hybridization properties of some (2'S)-2'-deoxy-2'-C-methyloligonucleotides with pyrimidine bases [10] [11] and their enhanced stability towards purified nucleases, human serum, and human cellular extracts have been reported [12]. Therefore, the preparation of the corresponding purine phosphoramidites seems to be a desirable objective.…”

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confidence: 99%

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