Synthesis of phosphorodithioate RNA by the H-phosphonothioate method

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4451-4454

  Greef, Charles H ^a   Seeberger, Peter H ^a   Caruthers, Marvin H ^a   Beaton, Graham ^b   Bankaitis Davis, Danute ^b  

^a UNIVERSITY OF COLORADO   (United States)

^b AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHORODITHIOIC ACID DERIVATIVE;

ANALYTIC METHOD; ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROLYSIS; NONHUMAN; OXIDATION; REACTION ANALYSIS; RNA TRANSCRIPTION;

EID: 0030600170     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00882-9     Document Type: Article

References (15)

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10. 10. Syntheses were performed on an Applied Biosysterms 394 instrument. The automated cycle contained the following steps: i. Detritylation: a. 4 × 5s delivery 2% TCA/DCM. b. 20s rinse dichloromethane (DCM). ii. Coupling: a. 2 × 5s simultaneous delivery of monomer 3a-d at 0.1 M in 1:1 MeCN/pyridine and diphenylchlorophosphate at 0.1 M in 95:5 MeCN/pyridine with 10s wait following each delivery. b. 10s rinse with 1:1 MeCN/pyridine. iii. Oxidation: a. 2 × 30s simultaneous delivery of 2,4 dichlorobenzylthiosuccinimide at 0.1 M in DCM and 5% TEA/DCM with 45s wait following each delivery, b. 3 × 10s rinse with DCM iv. Capping: a. 1 × 20s delivery of capping reagents (followed by 20s wait). b. 2 × 10s rinse with DCM.
11. 11. Dreef, C. E.; Dreef-Tromp, C. M; Marel, G. A.v.d.; van Boom, J. J. Synlett 1990, 481-483.
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13. 13. Gasparutto, D.; Livache, T; Bazin, H.; Duplaa, A.-M.; Guy, A.; Khorlin; A.; Molko, D.; Roget, A.; Téoule, R. Nucleic Acids Res. 1992, 5159-5166.
14. 14. Look, G. C.; Holmes, C. P.; Chinn, J. P.; Gallop, M. A. J. Org. Chem. 1994, 59, 7588-7590.
15. 31P NMR were recorded usually overnight on a GE Omega 300 MHz instrument. Spectra were referenced to 85% phosphoric acid.