Design of supported organocatalysts from a biomass-derived difuran compound and catalytic assessment for lactose hydrolysis

Chang, Hochan; Stamoulis, Alexios G.; Huber, George W.; Dumesic, James A.

doi:10.1039/d2gc04243f

Design of supported organocatalysts from a biomass-derived difuran compound and catalytic assessment for lactose hydrolysis

Journal Article · Tue Dec 26 23:00:00 EST 2023 · Green Chemistry

DOI:https://doi.org/10.1039/d2gc04243f· OSTI ID:2420318

^[1]; Stamoulis, Alexios G. ^[2]; ^[2]; ^[3]

Univ. of Wisconsin, Madison, WI (United States); OSTI
Univ. of Wisconsin, Madison, WI (United States)
Univ. of Wisconsin, Madison, WI (United States); Great Lakes Bioenergy Research Center (GLBRC), Madison, WI (United States)

The engineered structures and active sites of enzyme catalysts give rise to high catalytic activity and selectivity toward desired reactions. We have employed a biomass-derived difuran compound to append N-substituted maleimides with amino acid (glutamic acid) substitution by Diels–Alder reaction to mimic the chemical functional groups that comprise the active site channels in enzyme catalysts. The difunctionality of the biomass-derived difuran allows production of Diels–Alder adducts by appending two amino acid moieties to form a difunctional organocatalyst. The catalytic activity of the organocatalyst can be improved by immobilizing the organocatalyst on solid supporting materials. Accordingly, the structures of these immobilized organocatalysts can be engineered to mimic enzymatic active sites and to control the interaction between reactants, products, and transition states of catalytic reactions. Lactose hydrolysis was carried out to provide an example of industrial application of this approach to design and fabricate new supported organocatalysts as artificial enzymes.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Wisconsin, Madison, WI (United States)

Sponsoring Organization:: USDOE Office of Science (SC); National Institutes of Health (NIH); National Science Foundation (NSF)

Grant/Contract Number:: SC0014058; SC0018409

OSTI ID:: 2420318

Journal Information:: Green Chemistry, Journal Name: Green Chemistry Journal Issue: 5 Vol. 25; ISSN GRCHFJ; ISSN 1463-9262

Publisher:: Royal Society of ChemistryCopyright Statement

Country of Publication:: United States

Language:: English

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