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| Predicate | Object |
|---|---|
| rdf:type | |
| lifeskim:mentions | |
| pubmed:issue |
4
|
| pubmed:dateCreated |
1994-4-7
|
| pubmed:abstractText |
The three-dimensional structure of 4'-azidothymidine has been determined for the solid state and in solution. X-ray crystal analysis indicates the presence of two independent molecules (A and B) having the following conformational parameters: Phase angles, PA = 13.7 degrees, PB = 12.6 degrees (C3'-endo envelope); puckering amplitude psi mA = 32.4 degrees, psi mB = 37.2 degrees; glycosyl torsion angle chi A = -88.2 degrees, chi B = -71.2 degrees; 4'-5' torsion angle gamma A = 58.5 degrees, gamma B = 36.0 degrees. The solution conformation was determined from NMR coupling constants in D2O. Analysis using the computer programs PSEUROT and DAERM yielded phase angles (P) of 53.2 degrees (C4'-exo envelope) (major conformer) and 63 degrees (C4'-exo envelope), respectively, with corresponding puckering amplitudes (psi m) of 34.9 degrees and 45.8 degrees. A gated 13C NMR experiment was used to determine the 1H-13C vicinal coupling constants used to calculate the solution glycosyl torsion angle (chi) to be either -80 degrees or -160 degrees and a 4'-5' torsion angle, gamma, of ca. 180 degrees. These studies show that 4'-azidothymidine is conformationally exceptional among the antiretroviral nucleosides both as a solid and in solution. The C3'-endo (northern) conformation determined by X-ray crystallography is rare among HIV-inhibitory nucleosides which usually exist in the solid state in a southern conformation. The solution structure is even more peculiar in that it exists in the extremely rare 4'-exo envelope conformation.
|
| pubmed:language |
eng
|
| pubmed:journal | |
| pubmed:citationSubset |
IM
|
| pubmed:chemical | |
| pubmed:status |
MEDLINE
|
| pubmed:month |
Feb
|
| pubmed:issn |
0022-2623
|
| pubmed:author | |
| pubmed:issnType |
Print
|
| pubmed:day |
18
|
| pubmed:volume |
37
|
| pubmed:owner |
NLM
|
| pubmed:authorsComplete |
Y
|
| pubmed:pagination |
431-8
|
| pubmed:dateRevised |
2005-11-17
|
| pubmed:meshHeading |
pubmed-meshheading:8120862-Antiviral Agents,
pubmed-meshheading:8120862-Crystallography, X-Ray,
pubmed-meshheading:8120862-HIV,
pubmed-meshheading:8120862-Magnetic Resonance Spectroscopy,
pubmed-meshheading:8120862-Molecular Conformation,
pubmed-meshheading:8120862-Stereoisomerism,
pubmed-meshheading:8120862-Zidovudine
|
| pubmed:year |
1994
|
| pubmed:articleTitle |
Solid-state and solution conformations of the potent HIV inhibitor, 4'-azidothymidine.
|
| pubmed:affiliation |
Institute of Bio-Organic Chemistry, Syntex Discovery Research, Palo Alto, California 94304.
|
| pubmed:publicationType |
Journal Article
|