5'-Deoxy-5'-thioribonucleoside-5'-triphosphates

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 1021-1024

  Patel, Bhisma Kumar ^a   Eckstein, Fritz ^a  

^a MAX PLANCK INSTITUTE OF EXPERIMENTAL MEDICINE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

5' DEOXY 5' THIOADENOSINE 5' TRIPHOSPHATE; 5' DEOXY 5' THIOURIDINE 5' TRIPHOSPHATE; NUCLEOSIDE DERIVATIVE; NUCLEOSIDE TRIPHOSPHATE; RNA POLYMERASE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIOPHAGE T7; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; RNA SYNTHESIS;

EID: 0031562067     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00084-1     Document Type: Article

References (26)

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16. 31P NMR spectrum.
17. 2). Even after purification the product was contaminated with a small quantity of pyrophosphate δP = -10.
18. 2),
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20. β)].
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22. 2O) 16.9 (s)]. 5′-Deoxy-5′-thioribonucleotide-5′-monophosphate 5 is a substrate for alkaline phosphatase and is degraded to 5′-thio-5′-deoxyadenosine.
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24. 20. To a vigorously stirred solution of 4 or 5 (26 mmol) in N,N′-dimethylformamide (0.5 mL), tri-n-butylamine (18.74 μl, 78 mmol) was added under an argon atmosphere. To this solution N,N′-carbonyldiimidazole (21 mg, 130 mmol) in N,N′-dimethylformamide (0.5 mL) was added and stirring was continued at RT for 4hr. Methanol (8.4 μl) was added followed by addition of tri-n-butyl ammonium pyrophosphate (119 mg, 130 mmol) in N,N′-dimethylformamide (200 μl) after 0.5 h. The reaction mixture was stirred at room temperatute for 20 hr. The reaction mixture was filtered to remove the imidazolium pyrophosphate, followed by addition of an equal volume of methanol, evaporation to dryness in vacuo. The residue was redissolved in water (2 mL) and purified by chromatography over DEAE-A-25-sephadex using a linear gradient of TEAB (0 - 0.4 M, total volume 2 1) followed by preperative HPLC (buffer system and gradent as in foot note 16) to yield the products.
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26. 22. Full length transcripts were observed even in the presence of only three nucleoside 5′-triphosphates, presumably by misincorporation. This was not observed when either 6 or 7 were also present in the transcription mixture. It thus appears that these compounds act as inhibitors of misincorporation.