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Abstract:

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.

Registro:

Documento: Artículo
Título:Synthesis and properties of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl oligonucleotides
Autor:Cicero, D.O.; Gallo, M.; Neuner, P.J.; Iribarren, A.M.
Filiación:Istituto Di Ricerche Di Biologia Molecolare P. Angeletti, Via Pontina Km. 30, 600, 00040-Pomezia, Rome, Italy
Instituto De Investigaciones En Ingeniería Genética Y Biología Molecular, Vuelta de Obligado 2490 2P, 1428 Buenos Aires, Argentina
Universidad Nacional De Quilmes, Roque Sáenz Peña 180, Bernal, 1876 Pcia. de Buenos Aires, Argentina
Instituto De Investigaciones En Ingenieria, Genética Y Biología Molecular, Vuelta de Obligado 2490 2P, 1428 Buenos Aires, Argentina
Palabras clave: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
Año:2001
Volumen:57
Número:36
Página de inicio:7613
Página de fin:7621
DOI: http://dx.doi.org/10.1016/S0040-4020(01)00745-1
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v57_n36_p7613_Cicero

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Citas:

---------- APA ----------
Cicero, D.O., Gallo, M., Neuner, P.J. & Iribarren, A.M. (2001) . Synthesis and properties of (2′S)- and (2′R)-2′-deoxy-2′-C-methyl oligonucleotides. Tetrahedron, 57(36), 7613-7621.
http://dx.doi.org/10.1016/S0040-4020(01)00745-1
---------- CHICAGO ----------
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" . Tetrahedron 57, no. 36 (2001) : 7613-7621.
http://dx.doi.org/10.1016/S0040-4020(01)00745-1
---------- MLA ----------
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" . Tetrahedron, vol. 57, no. 36, 2001, pp. 7613-7621.
http://dx.doi.org/10.1016/S0040-4020(01)00745-1
---------- VANCOUVER ----------
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. Tetrahedron. 2001;57(36):7613-7621.
http://dx.doi.org/10.1016/S0040-4020(01)00745-1