Synthesis and properties of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl oligonucleotides
The synthesis of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl-N3-(4-t-butylbenzoyl) uridine, (2′S)-2′-deoxy-2′-C-methyluridine and (2′S)-2′-deoxy-2′-C-methyl-N4-isobutyryl cytidine building blocks are here described. The preparation of oligonucleotides carrying these monomers in all positions but 3′-end is...
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todo:paper_00404020_v57_n36_p7613_Cicero2023-10-03T14:50:39Z Synthesis and properties of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl oligonucleotides Cicero, D.O. Gallo, M. Neuner, P.J. Iribarren, A.M. 2′-deoxy-2′-C-alkylnucleotides Antisense Hybridization properties Modified oligonucleotides 2' deoxy 2' c methyl n 3 (4 tert butylbenzoyl)uridine 2' deoxy 2' c methyl n 4 isobutyrylcytidine 2' deoxy 2' c methyloligonucleotide derivative 2' deoxy 2' c methyluridine 3',5' o (tetraisopropyldisiloxane 1,3 diyl) 2' deoxy 2' c methyl n 4 isobutyrylcytidine 5' o dimethoxytrityl 2' deoxy 2' c methyl n 3 (4 tert butylbenzoyl)uridine 3' o (2 cyanoethyl n,n diisopropylphosphoramidite) 5' o dimethoxytrityl 2' deoxy 2' c methyl n 4 isobutyrylcytidine 3' o (2 cyanoethyl n,n diisopropylphosphoramidite) 5' o dimethoxytrityl 2' deoxy 2' c methyluridine 3' o (2 cyanoethyl n,n diisopropylphosphoramidite) complementary DNA monomer oligonucleotide unclassified drug article binding affinity chemical reaction conformational transition DNA hybridization drug structure drug synthesis hybrid melting point priority journal reaction analysis RNA hybridization RNA sequence The synthesis of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl-N3-(4-t-butylbenzoyl) uridine, (2′S)-2′-deoxy-2′-C-methyluridine and (2′S)-2′-deoxy-2′-C-methyl-N4-isobutyryl cytidine building blocks are here described. The preparation of oligonucleotides carrying these monomers in all positions but 3′-end is presented and the binding affinity between these new fragments and the complementary DNA and RNA sequences is also assessed. (2′R) substituted oligonucleotides did not hybridize with either the complementary DNA or RNA sequences. However, the first derivative of melting curves of hybrids containing (2′S) modified oligonucleotides indicated melting transitions. © 2001 Elsevier Science Ltd. All rights reserved. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00404020_v57_n36_p7613_Cicero |
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Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
2′-deoxy-2′-C-alkylnucleotides Antisense Hybridization properties Modified oligonucleotides 2' deoxy 2' c methyl n 3 (4 tert butylbenzoyl)uridine 2' deoxy 2' c methyl n 4 isobutyrylcytidine 2' deoxy 2' c methyloligonucleotide derivative 2' deoxy 2' c methyluridine 3',5' o (tetraisopropyldisiloxane 1,3 diyl) 2' deoxy 2' c methyl n 4 isobutyrylcytidine 5' o dimethoxytrityl 2' deoxy 2' c methyl n 3 (4 tert butylbenzoyl)uridine 3' o (2 cyanoethyl n,n diisopropylphosphoramidite) 5' o dimethoxytrityl 2' deoxy 2' c methyl n 4 isobutyrylcytidine 3' o (2 cyanoethyl n,n diisopropylphosphoramidite) 5' o dimethoxytrityl 2' deoxy 2' c methyluridine 3' o (2 cyanoethyl n,n diisopropylphosphoramidite) complementary DNA monomer oligonucleotide unclassified drug article binding affinity chemical reaction conformational transition DNA hybridization drug structure drug synthesis hybrid melting point priority journal reaction analysis RNA hybridization RNA sequence |
| spellingShingle |
2′-deoxy-2′-C-alkylnucleotides Antisense Hybridization properties Modified oligonucleotides 2' deoxy 2' c methyl n 3 (4 tert butylbenzoyl)uridine 2' deoxy 2' c methyl n 4 isobutyrylcytidine 2' deoxy 2' c methyloligonucleotide derivative 2' deoxy 2' c methyluridine 3',5' o (tetraisopropyldisiloxane 1,3 diyl) 2' deoxy 2' c methyl n 4 isobutyrylcytidine 5' o dimethoxytrityl 2' deoxy 2' c methyl n 3 (4 tert butylbenzoyl)uridine 3' o (2 cyanoethyl n,n diisopropylphosphoramidite) 5' o dimethoxytrityl 2' deoxy 2' c methyl n 4 isobutyrylcytidine 3' o (2 cyanoethyl n,n diisopropylphosphoramidite) 5' o dimethoxytrityl 2' deoxy 2' c methyluridine 3' o (2 cyanoethyl n,n diisopropylphosphoramidite) complementary DNA monomer oligonucleotide unclassified drug article binding affinity chemical reaction conformational transition DNA hybridization drug structure drug synthesis hybrid melting point priority journal reaction analysis RNA hybridization RNA sequence Cicero, D.O. Gallo, M. Neuner, P.J. Iribarren, A.M. Synthesis and properties of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl oligonucleotides |
| topic_facet |
2′-deoxy-2′-C-alkylnucleotides Antisense Hybridization properties Modified oligonucleotides 2' deoxy 2' c methyl n 3 (4 tert butylbenzoyl)uridine 2' deoxy 2' c methyl n 4 isobutyrylcytidine 2' deoxy 2' c methyloligonucleotide derivative 2' deoxy 2' c methyluridine 3',5' o (tetraisopropyldisiloxane 1,3 diyl) 2' deoxy 2' c methyl n 4 isobutyrylcytidine 5' o dimethoxytrityl 2' deoxy 2' c methyl n 3 (4 tert butylbenzoyl)uridine 3' o (2 cyanoethyl n,n diisopropylphosphoramidite) 5' o dimethoxytrityl 2' deoxy 2' c methyl n 4 isobutyrylcytidine 3' o (2 cyanoethyl n,n diisopropylphosphoramidite) 5' o dimethoxytrityl 2' deoxy 2' c methyluridine 3' o (2 cyanoethyl n,n diisopropylphosphoramidite) complementary DNA monomer oligonucleotide unclassified drug article binding affinity chemical reaction conformational transition DNA hybridization drug structure drug synthesis hybrid melting point priority journal reaction analysis RNA hybridization RNA sequence |
| description |
The synthesis of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl-N3-(4-t-butylbenzoyl) uridine, (2′S)-2′-deoxy-2′-C-methyluridine and (2′S)-2′-deoxy-2′-C-methyl-N4-isobutyryl cytidine building blocks are here described. The preparation of oligonucleotides carrying these monomers in all positions but 3′-end is presented and the binding affinity between these new fragments and the complementary DNA and RNA sequences is also assessed. (2′R) substituted oligonucleotides did not hybridize with either the complementary DNA or RNA sequences. However, the first derivative of melting curves of hybrids containing (2′S) modified oligonucleotides indicated melting transitions. © 2001 Elsevier Science Ltd. All rights reserved. |
| format |
JOUR |
| author |
Cicero, D.O. Gallo, M. Neuner, P.J. Iribarren, A.M. |
| author_facet |
Cicero, D.O. Gallo, M. Neuner, P.J. Iribarren, A.M. |
| author_sort |
Cicero, D.O. |
| title |
Synthesis and properties of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl oligonucleotides |
| title_short |
Synthesis and properties of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl oligonucleotides |
| title_full |
Synthesis and properties of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl oligonucleotides |
| title_fullStr |
Synthesis and properties of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl oligonucleotides |
| title_full_unstemmed |
Synthesis and properties of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl oligonucleotides |
| title_sort |
synthesis and properties of (2′s)- and (2′r)-2′-deoxy-2′-c-methyl oligonucleotides |
| url |
http://hdl.handle.net/20.500.12110/paper_00404020_v57_n36_p7613_Cicero |
| work_keys_str_mv |
AT cicerodo synthesisandpropertiesof2sand2r2deoxy2cmethyloligonucleotides AT gallom synthesisandpropertiesof2sand2r2deoxy2cmethyloligonucleotides AT neunerpj synthesisandpropertiesof2sand2r2deoxy2cmethyloligonucleotides AT iribarrenam synthesisandpropertiesof2sand2r2deoxy2cmethyloligonucleotides |
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1807316341029339136 |