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• W2079079332 abstract "The conformations of the antimitotic agent taxol and its side chain methyl ester have been studied by NMR-spectroscopy and molecular modeling in hydrophobic (CDCl3) and hydrophilic (water, d6-DMSO) solvents. For the side chain methyl ester (4), the coupling constant JH2′-H3′ changes from ≈2 Hz in chloroform to ≈5 Hz in d6-DMSO or water : d6-DMSO, 1 : 1 (v/v). The conformational equilibrium for 4 thus shifts from one favoring conformers with a gauche <H-C2′-C3′-H> torsion angle (chloroform), to one predominantly of conformers having this torsion angle anti. In the case of taxol, JH2′-H3′ changes from 2.7 Hz in CDCl3 to ≈8 Hz in water, water - sodium dodecyl sulfate (SDS) and/or d6-DMSO. Again, gauche conformations are implicated in chloroform, but molecular modeling suggests the anti conformer 27 to be dominant in aqueous media and in d6-DMSO. No nuclear Overhauser effects (nOe's) between the side chain and the taxane ring-system are observed in chloroform solution. In water and/or d6-DMSO, however, nOe's between the side chain (Ph3′ and H2′) and the OAc4 methyl group are detected." @default.
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• W2079079332 date "1993-07-01" @default.
• W2079079332 modified "2023-09-27" @default.
• W2079079332 title "NMR and molecular modeling study of the conformations of taxol and of its side chain methylester in aqueous and non-aqueous solution." @default.
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• W2079079332 doi "https://doi.org/10.1016/s0040-4020(01)81823-8" @default.
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