A new method for oligonucleotide derivatization of the 3' or 5'- termini with a CPG-support carrying the natural product isoargentatin-D

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6123-6126

  Gaytán, Paul ^a   Yañez, Jorge ^a   Soberón, Xavier ^a   Martínez, Robert ^b  

^a INSTITUTO DE CIENCIAS FÍSICAS   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

OLIGONUCLEOTIDE; PHOSPHORAMIDIC ACID DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; DERIVATIZATION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 17444439401     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01388-9     Document Type: Article

References (14)

1. Boutorin, A.S.; Gus'kova, L. V.; Ivanova, E. M.; Kobetz, N. D.; Zarytova, V. F.; Ryte, A. S.; Yurchenko, L. V.; Vlassov, V. V.; FEBS Lett. 1989, 254, 129-132.
2. Beaucage, S. L.; Radhakrishnan, P. I.; Tetrahedron 1993, 49, 1925-1963.
3. Reagents available from Glen Research Corporation. 44901 Falcon Place, Sterling, VA 20166, USA.
4. Romo de Vivar, A.; Martínez-Vazquez, M.; Matsubara, C.; Pérez-Sánchez, G.; Joseph-Nathan, P.; Phytochemistry 1990, 29, 915-918.
5. Isoargentin-B was obtained by hexane elution of a silicagel column chromatography previously charged with the acetonic extract of guayule.
6. For this analysis we used an analytical (4.6 × 250 mm) ODS column from Vydac and an isocratic run during 5 min of buffer A followed of a gradient from 0% to 30% of buffer B in 20min. The flow was setup at 1.2 ml/min. Buffer A was acetonitrile and buffer B was methanol.
7. 1H NMR analysis was performed at 300 MHz in a Varian Unity 300. The main difference between both epimers was found in the signals corresponding to H-3.
8. Alul, R. H.; Singman, C. H.; Zhang, G.; Letsinger, R. L.; Nucleic Acids. Res. 1991, 19, 1527-1532.
9. Sharma, P.; Sharma, A. K.; Malhotra, V. P.; Gupta, K. C.; Nucleic Acids. Res. 1992, 20, 4100.
10. Atkinson, T.; Smith, M.; Solid-phase Synthesis of Oligodeoxyribonucleotides by the Phosphite-triester Method. In Oligonucleotide Synthesis: a practical approach; Gait, M. J. Ed.; IRL press: Oxford, 1984; pp. 47-48.
11. Average coupling step with this phosphoramidite was 97%.
12. Average coupling step with this phosphoramidite was 98.5%.
13. Oligonucleotides were analyzed on an analytical (4.6 × 150 mm) ODS Spherisorb column from Beckman, with a flow of 1 ml/min. Buffer A was 0.1M triethylammonium acetate pH 7.0 and buffer B was acetonitrile. The run was carried out under next conditions: gradient of buffer B from 7% to 27% in 16 min, followed by an isocratic of 27% of buffer B during 8 min and a gradient of buffer B from 27% to 40% in 5 min.
14. PAGE analysis was performed in an analytical "tall mighty small" camera from Hoefer Scientific Instruments, employing a 30% polyacrylamide / 5M urea gel.