A biocatalytic approach for regioselective monoacetylation of 3-aryloxy-1,2-propanediols by porcine pancreatic lipase

Abstract

Among the various lipases screened for the regioselective monoacetylation of 3-aryloxy-1,2-propanediols, porcine pancreatic lipase was found to afford a higher yield. The selectivity for the monoacetylation process was maximized by using different organic solvents and diisopropyl ether gave the highest conversion to monoacetylated product (ca. 98%). The optimized reaction afforded excellent yields of the monoacetylated product with regioselectivity at the terminal hydroxyl group in the presence of various aryl substituents in the starting material.

Kinetics and mechanism of regioselective monoacetylation of 3-aryloxy-1,2-propandiols using immobilized Candida antarctica lipase

“…The conversion with Novozyme 435 and Lipase 135 Amano PS Amano was 99 and 86.6%, respectively and the 136 monoacetylated excess was above 95%. This study reports 137 improved conversion for monoacetylated product using 138 C. antarctica lipase compared to the of recent report by Meena 139 and Banerjee[22]. C. antarctica lipase B (CALB), a serine hydrolase, 140 is the most widely used biocatalyst for organic synthesis in lab 141 scale and industrial scale.…”

“…The enzymatic regioselective synthesis plays 30 vital role in pursuing asymmetric synthesis of active chiral 31 compounds. Lipase catalyzed regioselective monoacetylation has 32 been established as a suitable approach to obtain the mono-33 acetylated products using various diols [19][20][21][22]. Monoacetylated 34 derivatives of 1,2-diols can be subsequently used for synthesis of 35 enantiomerically pure diols via sequential kinetic resolution 36 [19].…”

“…16 Biocatalytic asymmetric synthesis offers great potential as an 17 alternative tool to chemical synthesis and provides a major path 18 for the synthesis of enantiomerically pure compounds through 19 kinetic resolution of racemic substrates or asymmetrization of 20 prochiral compounds [8][9][10][11][12][13][14]. The regioselective acetylation of 21 polyhydroxy compounds has been an interesting area of research 22 in chemistry for many years. The selective manipulation of 23 hydroxyl groups poses many challenges in synthesis of active 24 pharmaceutical intermediates [15][16][17].…”

“…nonspreading lubricants, resins, pigmented ink, polyesters and 57 optics [22,45]. 58 There have been no report on kinetics and mechanism of 59 regioslective monoacetylation of 3-aryloxy-1,2-propanediols 60…”