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Abstract:

A new stereoselective synthesis of 2′-C-methyluridine was carried out. The preparation of the corresponding protected phosphoramidite suitable for the automated synthesis of oligonucleotides, including the regioselective protection of the 2′-hydroxyl group, is described here. This new modified nucleotide is expected to generate RNA analogues potentially useful in applications where proper RNA folding is required since the 2′-hydroxyl is conserved. © 2001 Elsevier Science Ltd.

Registro:

Documento: Artículo
Título:2′-C-Methyluridine phosphoramidite: A new building block for the preparation of RNA analogues carrying the 2′-hydroxyl group
Autor:Gallo, M.; Monteagudo, E.; Cicero, D.O.; Torres, H.N.; Iribarren, A.M.
Filiación: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
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
Palabras clave:2′-C-alkylnucleotides; RNA analogues; Sugar conformation; 2' c methyluridine; 2' c methyluridine phosphoramidite; 3',5' di o acetyl 2' c methyluridine; 3',5' di o acetyl 2' o tetrahydropyranyl 2' c methyluridine; 3',5' o (tetraisopropyldisiloxane 1,3 diyl) 2' c methyluridine; 5' o dimethoxytrityl 2' c methyluridine 3 o (2 cyanoethyl n,n diisopropyl phosphoramidite); hydroxyl group; oligonucleotide; phosphoramidic acid derivative; RNA derivative; unclassified drug; uridine derivative; article; chemical modification; chemical reaction; chemical structure; priority journal; reaction analysis; stereochemistry; synthesis
Año:2001
Volumen:57
Número:27
Página de inicio:5707
Página de fin:5713
DOI: http://dx.doi.org/10.1016/S0040-4020(01)00484-7
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v57_n27_p5707_Gallo

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Citas:

---------- APA ----------
Gallo, M., Monteagudo, E., Cicero, D.O., Torres, H.N. & Iribarren, A.M. (2001) . 2′-C-Methyluridine phosphoramidite: A new building block for the preparation of RNA analogues carrying the 2′-hydroxyl group. Tetrahedron, 57(27), 5707-5713.
http://dx.doi.org/10.1016/S0040-4020(01)00484-7
---------- CHICAGO ----------
Gallo, M., Monteagudo, E., Cicero, D.O., Torres, H.N., Iribarren, A.M. "2′-C-Methyluridine phosphoramidite: A new building block for the preparation of RNA analogues carrying the 2′-hydroxyl group" . Tetrahedron 57, no. 27 (2001) : 5707-5713.
http://dx.doi.org/10.1016/S0040-4020(01)00484-7
---------- MLA ----------
Gallo, M., Monteagudo, E., Cicero, D.O., Torres, H.N., Iribarren, A.M. "2′-C-Methyluridine phosphoramidite: A new building block for the preparation of RNA analogues carrying the 2′-hydroxyl group" . Tetrahedron, vol. 57, no. 27, 2001, pp. 5707-5713.
http://dx.doi.org/10.1016/S0040-4020(01)00484-7
---------- VANCOUVER ----------
Gallo, M., Monteagudo, E., Cicero, D.O., Torres, H.N., Iribarren, A.M. 2′-C-Methyluridine phosphoramidite: A new building block for the preparation of RNA analogues carrying the 2′-hydroxyl group. Tetrahedron. 2001;57(27):5707-5713.
http://dx.doi.org/10.1016/S0040-4020(01)00484-7