Prof. Choong Eui SONG and his students (Department of Chemistry) successfully developed biomimetic catalytic transformation of toxic α-oxoaldehydes to high-value chiral α-hydroxythioesters using artificial glyoxalase I.
Prof. SONG, CHOONGEUI
Through millions of years of evolution, nature has accomplished the development of the ideal catalysts called enzymes that catalyze the biological chemical reactions necessary to sustain all life on Earth. Thus, lessons from how natural enzymatic systems operate can therefore be very important for the design of the more efficient and environmentally benign catalytic systems. Prof. Choong Eui SONG and his students (Department of Chemistry) successfully developed biomimetic catalytic transformation of toxic α-oxoaldehydes to high-value chiral α-hydroxythioesters using artificial glyoxalase I. This reaction is exceptionally enantioselective and the α-hydroxythioester products are of high value for multiple synthetic applications. The synthetic applicability was highlighted by the coupling reagent-free synthesis of several optically pure α-hydroxyamides, highly important drug candidates in the pharmaceutical industry. Moreover, his group made the important scientific discovery that water enables new catalytic reactions for otherwise unreactive substrate systems. Enantioselective Michael addition of extremely unreactive α,α-disubstituted β-nitroalkenes with malonate derivatives using hydrophobic catalysts, affording both enantiomers of highly enantio-enriched Michael adducts with all-carbon-substituted chiral quaternary centers, has been achieved for the first time. The reaction was made possible by the “on water condition,” which enables enforced hydrophobic interactions between catalysts and substrates due to hydrophobic hydration effects.
Developed water protocol was successfully applied for the scalable one-pot syntheses of chiral GABA analogues bearing all-carbon quaternary stereogenic centers at the β-position that might show highly interesting pharmaceutical properties. These results were recently published in the world top journals Nature Communications and Angewandte Chemie International Edition.
* Related papers: 1) “Biomimetic catalytic transformation of toxic-oxoaldehydes to high-value chiral α-hydroxythioesters using artificial glyoxalase I” – Nat.
Commun. 2017, 8, 14877. 2) “Water-enabled catalytic asymmetric Michael reactions of unreactive nitroalkenes: One-pot synthesis of chiral GABA-analogs with all-carbon quaternary stereogenic centers” – Angew. Chem. Int. Ed. 2017, 56, 1835 (as a Hot Paper).