d-Xylose and l-arabinose laurate esters: Enzymatic synthesis, characterization and physico-chemical properties

Abstract

Efficient enzymatic synthesis of d-xylose and l-arabinose lauryl mono- and diesters has been achieved by transesterification reactions catalysed by immobilized Candida antarctica lipase B as biocatalyst, in organic medium in the presence of d-xylose or l-arabinose and vinyllaurate at 50 °C. In case of l-arabinose, one monoester and one diester were obtained in a 57% overall yield. A more complex mixture was produced for d-xylose as two monoesters and two diesters were synthesized in a 74.9% global yield. The structures of all these pentose laurate esters was solved. Results demonstrated that the esterification first occurred regioselectively onto the primary hydroxyl groups. Pentose laurate esters exhibited interesting features such as low critical aggregation concentrations values all inferior to 25 μM. Our study demonstrates that the enzymatic production of l-arabinose and d-xylose-based esters represents an interesting approach for the production of green surfactants from lignocellulosic biomass-derived pentoses.

Enzymatic Synthesis of Glucose‐ and Xylose Laurate Esters Using Different Acyl Donors, Higher Substrate Concentrations, and Membrane Assisted Solvent Recovery

“…However, only a couple of the isolated compounds could be unequivocally identified as the diesters 2,5‐di‐ O ‐lauryl‐D‐xylofuranose and 3,5‐di‐ O ‐lauryl‐D‐xylofuranose, which have already been reported as two of the products formed during transesterification of xylose with vinyl laurate. [ 9 ] None of the products could be obtained in sufficient purity to be used as reliable standard for quantification. The formation of more ester products (regioisomers) during the (trans)esterification of xylose compared to glucose could be due to the higher tendency for acyl migration in this monosaccharide.…”

“…[ 4 ] The enzymatic acylation of pure glucose has been often reported in literature, [ 5–7 ] while xylose has remained a more underexplored substrate. [ 8,9 ] The synthesis of sugar esters directly from lignocellulosic biomass has also been reported in literature, although with very low conversions. [ 10 ]…”

Novozym 435: the “perfect” lipase immobilized biocatalyst?

“…The reaction used vinyl laurate and L-arabinose or D-xylose. 350 Using L-arabinose, a 57% overall yield of one monoester and one diester was achieved. Using D-xylose, a 74.9% global yield of modified products was achieved, but the reaction regioselectivity was lower and two monoesters and two diesters were synthesized.…”

“…Using D-xylose, a 74.9% global yield of modified products was achieved, but the reaction regioselectivity was lower and two monoesters and two diesters were synthesized. 350 Modification of lactulose with vinyl laurate was studied with 10 lipases. 351 N435 modified mainly the 1-Oposition, while Lipozyme TL-IM and Lipozyme RM-IM mainly modified the 6-O-position.…”

A green resin acid ester surfactant from colophony and xylitol: Synthesis, self‐assembly in nonaqueous solvents, and thermodynamics

“…It is also an intermediate metabolite in the human body and has good biocompatibility and biodegradability. Fatty acid xylitol esters are a class of nonionic surfactants with important physiological activities 8,9 . Some derivates have been shown to have antitumor activity 10 and plant growth inhibition 11 .…”