Enzymatic Preparation of a Homologous Series of Long-Chain 6-O-Acylglucose Esters and Their Evaluation as Emulsifiers

Abstract

Sugar fatty acid esters are nonionic surfactants that are widely exploited in the food and cosmetics industries, as well as in the oral care and medical supply fields. Accordingly, new methods for their selective synthesis and the "tuning" of their emulsifying properties are of considerable interest. Herein we report simple and irreversible enzymatic esterifications of d-glucose with seven fatty acid vinyl esters. The foaming and emulsifying effects of the resulting 6- O-acylglucose esters were then evaluated. In accord with expectations, when the length of the alkyl side chain associated with the 6- O-acylglucose esters increases, then their hydrophilic-lipophilic balance (HLB) values decrease, while the stabilities of the derived emulsions improve. In order to maintain good foaming properties, alkyl side chains of at least 9 to 11 carbons in length are required. In the first such assays on 6- O-acylglucose esters, most of those described herein are shown to be nontoxic to the HepG2, MCF-7, LNacp, SW549, and LO-2 cell lines.

Novozym 435: the “perfect” lipase immobilized biocatalyst?

“…347 6-O-Acylglucose esters have been produced by N435 catalyzed esterifications between D-glucose and seven different fatty acid vinyl esters which were used as emulsifiers. 348 N435 was one of the few biocatalysts with activity in the production of (3R,6R)-6-acetoxy-7-hydroxylinalool or (3R,6S)-6-acetoxy-7hydroxylinalool via esterification of 6,7-dihydroxy-linalool stereoisomers. 349 Transesterification has also been used for this purpose.…”

Synthesis and Evaluation of Saccharide-Based Aliphatic and Aromatic Esters as Antimicrobial and Antibiofilm Agents

“…Finally, although some of the sugar-based esters here presented have already been published for other applications and also as possible antibacterial agents [22][23][24][29][30][31][32][33], a detailed comparative study concerning the properties of a relative large number of both aliphatic and aromatic amphiphilic carbohydrate esters as antimicrobial (Gram-positive, Gram-negative, and fungi) and mostly antibiofilm agents is still lacking.…”

“…In these few cases, chemical esterification could be the main road to explore. Among all sugar-based surfactants, sucrose and glucose esters are the most studied and applied derivatives [21][22][23][24], while other derivatives, such as lactose esters, which can be easily obtained from waste whey, and mannose esters, have received less attention.…”

Singe cell oil (SCO) based bioactive compounds: II. Enzymatic synthesis of glucose fatty acid esters using SCOs as acyl group-donors and their biological activities

“…Different types of sugars (e.g. sucrose, fructose, glucose and lactose) can be used as acyl-acceptors to produce SEs by esterification with FAs or transesterification with FA esters as acyl-donors [7–9]. Glucose, a cheap and broadly available carbohydrate, having only one primary hydroxyl group, which predetermines a highly regioselective synthesis of SEs called glucose fatty acid esters (GEs) [10, 11].…”