2 research outputs found
One-Pot, Two-Module Three-Step Cascade To Transform Phenol Derivatives to Enantiomerically Pure (<i>R</i>)- or (<i>S</i>)‑<i>p</i>‑Hydroxyphenyl Lactic Acids
Readily available phenol derivatives
were substituted in <i>para</i>-position via a C–C
bond formation to give enantiomerically
pure (<i>R</i>)- or (<i>S</i>)-3-(<i>para</i>-hydroxyphenyl) lactic acids. The transformation was achieved by
designing a biocatalytic cascade consisting of three linear steps,
namely, (i) the C–C coupling of the phenol and pyruvate in
the presence of ammonia to afford the corresponding l-tyrosine
derivative, followed by (ii) oxidative deamination and (iii) enantioselective
reduction. Compatibility analysis showed that the reaction rate of
the first step is slowed in the presence of the product of the third
step; consequently, the three-step cascade was subdivided in two modules
(module 1 = step 1; module 2 = steps 2 and 3), which were run in one
pot sequentially. Because of the exquisite selectivity achieved in
the C–C coupling step, <i>para</i>-isomers were obtained
exclusively. By choosing the appropriate alcohol dehydrogenase, the
(<i>R</i>)- as well as the (<i>S</i>)-isomer were
isolated in enantiopure form. Preparative transformations of 2-, 3-,
and 2,3-disubstituted phenols (23–96 mM) afforded the corresponding
(<i>R</i>)- and (<i>S</i>)-<i>para</i>-hydroxyphenyl lactic acids in high yield (58%–85%) and enantiopure
form (<i>ee</i> > 97%)
MOESM1 of In vivo plug-and-play: a modular multi-enzyme single-cell catalyst for the asymmetric amination of ketoacids and ketones
Additional file 1. Additional table and figures