Enantiopurity and absolute configuration determination of arene cis‐dihydrodiol metabolites and derivatives using chiral boronic acids |
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| Authors: | Derek R. Boyd Narain D. Sharma Peter A. Goodrich John F. Malone Gareth McConville John S. Harrison Paul J. Stevenson Christopher C.R. Allen |
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| Affiliation: | 1. School of Chemistry and Chemical Engineering, Queen's University, Belfast, UK;2. School of Biological Sciences and Institute for Global and Food Security, Queen's University, Belfast, UK |
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| Abstract: | The relative merits of the methods employed to determine enantiomeric excess (ee) values and absolute configurations of chiral arene and alkene cis‐1,2‐diol metabolites, including boronate formation, using racemic or enantiopure (+) and (?)‐2‐(1‐methoxyethyl)phenylboronic acid (MEPBA), are discussed. Further applications of: 1) MEPBA derived boronates of chiral mono‐ and poly‐cyclic arene cis‐dihydrodiol, cyclohex‐2‐en‐1‐one cis‐diol, heteroarene cis/trans‐2,3‐diol, and catechol metabolites in estimating their ee values, and 2) new chiral phenylboronic acids, 2‐[1‐methoxy‐2,2‐dimethylpropyl]phenyl boronic acid (MDPBA) and 2‐[1‐methoxy‐1‐phenylmethyl]phenyl boronic acid (MPPBA) and their advantages over MEPBA, as reagents for stereochemical analysis of arene and alkene cis‐diol metabolites, are presented. |
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| Keywords: | asymmetric synthesis bacterial metabolism boronate diastereomers boronic acid enantiomers cis‐1,2‐diol bioproducts enantiomeric excess values |
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