4-Octyl
itaconate is a novel antiviral and immunoregulatory small
molecule showing great potential in the treatment of various autoimmune
diseases and viral infections. It is difficult to selectively esterify
the C4 carboxyl group of itaconate acid via one-step direct esterification
using chemical catalysts, while the two-step route with itaconic anhydride
as an intermediate is environmentally unfriendly and costly. This
research investigated the one-step and green synthesis of 4-octyl
itaconate through the structure control of lipase, obtaining 4-octyl
itaconate with over 98% yield and over 99% selectivity. Multiscale
molecular dynamics simulations were applied to investigate the reaction
mechanism. The cavity pocket of lipases resulted in a 4-octyl itaconate
selectivity by affecting distribution of substrates toward the catalytic
site. Toluene could enhance monoesterification in the C4 carboxyl
group and contribute to a nearly 100% conversion from itaconate acid
into 4-octyl itaconate by adjusting the catalytic microenvironment
around the lipase, producing a shrinkage effect on the channel.
Intralipid is wildly used in parenteral nutrition, providing energy and essential fatty acids for postoperative patients (Meguid et al., 1989).When the intralipid was injected into the vein, lipoprotein lipase was located in the endothelium, hydrolyzing triglyceride into sn-2 monoglyceride and fatty acid, which would be absorbed and metabolized by the skeletal muscle, cardiac muscle, liver cells, and adipose cells (Nguyen et al., 2008). The metabolic absorption and endogenous synthesis of majority lipids occur in the liver (Huang
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