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Simple synthetic route to an enzyme-inspired transesterification catalyst
Kumar, Ashwani1; Nothling, Mitchell D.2; Aitken, Heather M.1; Xiao, Zeyun3; Lam, Matthew4; Bell, Craig A.5,6; O'Mara, Megan L.1; Connal, Luke A.1
2022-10-11
摘要Inspired by the chemical structure of chymotrypsin, we report an artificial catalytic triad with high catalytic efficiency for the transesterification reaction of vinyl trifluoroacetate and methanol. Rate accelerations of (k(cat)/k(unc)) 4.81 x 10(4)-fold over the background reaction were observed. We highlight a simple two step synthetic approach to incorporate three functional groups (-OH, -CO2H, -imidazole) on a single molecule, similar to native enzymes like chymotrypsin. The addition of a hydrophobic chain furnishes amphiphilic catalysts that form clusters for reactions in organic solvents. The cluster formation was studied using molecular dynamics (MD) simulations, dynamic light scattering (DLS) and H-1 NMR, revealing complex H-bonding interactions between the catalytic head groups of the artificial catalytic triad, drawing similarities to native enzymes.
DOI10.1039/d2cy00744d
发表期刊CATALYSIS SCIENCE & TECHNOLOGY
ISSN2044-4753
页码5
通讯作者Connal, Luke A.(luke.connal@anu.edu.au)
收录类别SCI
WOS记录号WOS:000877639500001
语种英语