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Volumn 61, Issue 3, 1996, Pages 895-902

Potential lipophilic nucleotide prodrugs: Synthesis, hydrolysis, and antiretroviral activity of AZT and d4T acyl nucleotides

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOTIDE DERIVATIVE; PRODRUG; RNA DIRECTED DNA POLYMERASE; STAVUDINE DERIVATIVE; UNCLASSIFIED DRUG; ZIDOVUDINE DERIVATIVE;

EID: 0030049336     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951354p     Document Type: Article
Times cited : (39)

References (36)
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    • Hydrolysis of acetyl phosphate into acetyl and phosphate requires 3-6 kcal less than that of ATP to ADP (see: Biol Chem.: Mahler, H. R., Cordes, E. H., Eds.; Harper Int : New York, 1963; p 201).
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    • note
    • The purity of acyl nucleotides 1-5 was checked by reverse phase HPLC and typically ranged between 98-100% for acyl nucleotide in the triethylammonium form, and 90-95% for products in the sodium form, after exchange on Dowex AG50 WX8. Recently we found that precipitation of the acyl nucleotide triethylammonium salt, dissolved in the minimum methanol at 0 °C. by addition of a 1 M NaI acetone solution followed by extensive washing with cold acetone, allowed the isolation of the acyl nucleotide sodium salt without detectable decomposition. However, these products slowly decomposed even at -18 °C.
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    • note
    • 2O.
  • 26
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    • note
    • 31P chemical shift.
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    • note
    • It should be noted that the data obtained with cells infected by HIV2 confirm the data presented here and are not described in this paper for clarity purpose.
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    • note
    • The organic layer contains mainly 5′-acyl nucleoside. After evaporation, Zemplen deacylation, and silica gel flash chromatography, 20-40% starting nucleoside could be recovered.
  • 36
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    • note
    • 31P NMR spectra.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.