Journal of Biotechnology 64 (1998) 231 – 237 Lipase-catalyzed synthesis of arylaliphatic esters of -D( + )-glucose, n -alkyl- and arylglucosides and characterization of their surfactant properties Ralf T. Otto a,b , Uwe T. Bornscheuer b , Christoph Syldatk a , Rolf D. Schmid b, * a Institut fu ¨r Bioerfahrenstechnik, Uniersita ¨t Stuttgart, Allmandring 31, D-70569 Stuttgart, Germany b Institut fu ¨r Technische Biochemie, Uniersita ¨t Stuttgart, Allmandring 31, D-70569 Stuttgart, Germany Received 30 March 1998; received in revised form 17 July 1998; accepted 29 July 1998 Abstract -D( +)-Glucose, n -alkyl--D( +)-glucosides, salicin and 1-phenylglucoside were regioselectively acylated at the primary hydroxy group of the sugar moiety with a variety of non-activated arylaliphatic carboxylic acids using lipase B from Candida antarctica in a mainly solid phase in the presence of a small amount of t -butanol in yields up to 71%. The arylaliphatic glucose esters were highly water soluble (15 to 100 g l -1 ) and showed surface activity. Critical micellar concentrations between 2 and 95 mM and minimal surface tensions around 35–45 mN m -1 were determined. The hydrophilic – lypophilic balance values of arylaliphatic esters from -D( +)-glucose indicate a use in oil-in-water emulsions or detergents, whereas the n -alkyl- and arylglycosides can be employed as wetting agents or water-in-oil emulsifiers. © 1998 Elsevier Science B.V. All rights reserved. Keywords: Glucose; Salicin; Lipase; Candida antarctica ; Detergent 1. Introduction Surfactants and emulsifiers are widely used in the pharmaceutical, cosmetic, petroleum and food industries. Surfactant and emulsification proper- ties result from the presence of both hydrophilic and hydrophobic regions on the same molecule. Most compounds are synthesized chemically, however also surface-active molecules of biologi- cal origin obtained by bioprocesses as well as enzymatic synthesis have been described. Their properties are comparable to chemically prepared surfactants, but they also comprise a production from renewable-resource substrates and the ad- vantage of biodegradability (Fiechter, 1992). Aliphatic carbohydrate fatty acid esters are nonionic surfactants and are used e.g. as low-fat * *Corresponding author. Tel.: +49 711 6853193; fax: +49 711 6853196; e-mail: itbrsc@po.uni-stuttgart.de 0168-1656/98/$ - see front matter © 1998 Elsevier Science B.V. All rights reserved. PII S0168-1656(98)00125-4