TY - JOUR
T1 - Regioselective synthesis of lactulose esters by candida antarctica and thermomyces lanuginosus lipases
AU - Chávez-Flores, Luis F.
AU - Beltran, Hiram Isaac
AU - Arrieta-Baez, Daniel
AU - Reyes-Duarte, Dolores
N1 - Publisher Copyright:
© 2017 by the authors. Licensee MDPI, Basel, Switzerland.
PY - 2017/9
Y1 - 2017/9
N2 - The interest in sugar esters as emulsifiers has been increasing in recent years because they have tunable surfactant properties that depend on the chain length of the fatty acid and the type of the sugar, covering a wide range of hydrophilic-lipophilic balance (HLB). In this work, ten biocatalysts were used for the transesterification reaction screening of lactulose, a prebiotic sugar, with vinyl laurate. The reactions were followed by thin layer chromatography (TLC) analysis, identifying two major monoesters mixtures defined as monoester fraction 1 and monoester fraction 2. Candida antarctica lipase B (Novozym 435) produces “monoester fraction 1”, while Thermomyces lanuginosus lipase (Lipozyme® TL IM) and Mucor miehei lipase (Lipozyme®) seem to produce the same “monoester fraction 2”. These three enzymes were selected as model biocatalysts for a kinetic study, and monoester fractions 1 and 2 from Novozym 435 and Lipozyme® TL IM, respectively, were used for product characterization. Monoester fraction 1 contained 86.9% of the major monoester in position 1-O-, and monoester fraction 2 contained 91.4% of 6′-O-. Although these lipases acylated three positions of lactulose, they mainly synthesize a monoester presenting regioselectivity. These results contribute to the study of the chemical structure diversity of biosurfactants to enhance their applications in foods, pharmaceutical products, and cosmetics.
AB - The interest in sugar esters as emulsifiers has been increasing in recent years because they have tunable surfactant properties that depend on the chain length of the fatty acid and the type of the sugar, covering a wide range of hydrophilic-lipophilic balance (HLB). In this work, ten biocatalysts were used for the transesterification reaction screening of lactulose, a prebiotic sugar, with vinyl laurate. The reactions were followed by thin layer chromatography (TLC) analysis, identifying two major monoesters mixtures defined as monoester fraction 1 and monoester fraction 2. Candida antarctica lipase B (Novozym 435) produces “monoester fraction 1”, while Thermomyces lanuginosus lipase (Lipozyme® TL IM) and Mucor miehei lipase (Lipozyme®) seem to produce the same “monoester fraction 2”. These three enzymes were selected as model biocatalysts for a kinetic study, and monoester fractions 1 and 2 from Novozym 435 and Lipozyme® TL IM, respectively, were used for product characterization. Monoester fraction 1 contained 86.9% of the major monoester in position 1-O-, and monoester fraction 2 contained 91.4% of 6′-O-. Although these lipases acylated three positions of lactulose, they mainly synthesize a monoester presenting regioselectivity. These results contribute to the study of the chemical structure diversity of biosurfactants to enhance their applications in foods, pharmaceutical products, and cosmetics.
KW - Biocatalysts
KW - Lactulose
KW - Lipases
KW - Prebiotic sugar
KW - Regioselectivity
KW - Sugar fatty acid esters
KW - Transesterification
UR - http://www.scopus.com/inward/record.url?scp=85028912255&partnerID=8YFLogxK
U2 - 10.3390/catal7090263
DO - 10.3390/catal7090263
M3 - Artículo
SN - 2073-4344
VL - 7
JO - Catalysts
JF - Catalysts
IS - 9
M1 - 263
ER -