Enzyme-Catalyzed Chemoselective Transesterification Reactions on Hydroxymethylated Phenolic Compounds

Enzymatic Synthesis of a Capsinoid by the Acylation of Vanillyl Alcohol with Fatty Acid Derivatives Catalyzed by Lipases

“…Furthermore, several lipases are known to selectively acylate a primary alcohol rather than phenol. 14,15) It was therefore expected that selective O-acylation of the aliphatic, but not aromatic, hydroxyl group in vanillyl alcohol would give a capsinoid.…”

Biocatalytic potential of Fusarium globulosum lipase in selective acetylation/deacetylation reactions and in ester synthesis

“…Enzymes have seldom been employed for chemoselective discrimination between the phenolic and alcoholic groups present in the same molecule. There is only one report in the literature (Parmar et al . 1999) where such selection was achieved with porcine pancreatic lipase (PPL) but the reaction took 120 h for completion.…”

“…The reaction with FGL reported in the present work was much faster as it took only 12 h and, moreover, FGL can be produced economically in large quantities in comparison to PPL. These compounds are novel precursors for the synthesis of phenyl alkyl carbinols and aryl/alkyl chromanones, which are important bioactive compounds (Parmar et al . 1999).…”

“…This observed difference in specificity of the lipase could be due to a difference in the active site conformation of the enzyme. These selective deprotection reactions can find utility in the synthesis of various types of naturally occurring and biologically active benzopyranones (Parmar et al . 1999).…”

Synthesis of macromolecular systems via lipase catalyzed biocatalytic reactions: applications and future perspectives

“…Herein, a chemoenzymatic methodology has been designed and developed to make PEGylated curcumin derivatives as water soluble drug candidates with enhanced aqueous solubility and bioavailability. For this, the curcumin diester 81 was copolymerized with poly(ethylene glycol) (82) using Novozym 435 under solventless conditions (Scheme 19 Copolymer 83a induces Nrf2-driven NQO1 expression in a concentration dependent manner.…”