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- W7393375 abstract "ConclusionsBiological macromolecules frequently being receptors of small molecule ligands such as drugs create a chiral molecular environment. They are themselves constructed from chiral building blocks and spatially arranged in handed conformations. Accordingly, enantiomers will be recognized as different species at the binding sites of such receptors. Some rare cases have been reported on the crystallographically determined binding mode of both enantiomers together with the protein.Usually quite distinct binding affinities are observed for both forms. However, since solvation/desolvation properties are identical in these cases the energy difference can been attributed to conformational differences of local interaction geometries. A more strained and thus less favorable binding configuration is detected for the less active enantiomer. The distinct immobilization of stereoisomers in the handed environment of a binding pocket can also be exploited in enzyme kinetics, e.g. to achieve more favorable metabolic stability of retro/inverse peptides or to succeed in chiral resolution of amines and alcohols with lipases. Further crystallographic work with carefully selected and optimized crystallization conditions will hopefully reveal a more detailed insight into the spatial discrimination of stereoisomers at the binding site of proteins." @default.
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- W7393375 date "2005-12-30" @default.
- W7393375 modified "2023-09-25" @default.
- W7393375 title "Differences in Binding of Stereoisomers to Protein Active Sites" @default.
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- W7393375 doi "https://doi.org/10.1007/0-306-48662-8_3" @default.
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