Efficient synthesis of a long carbohydrate chain alkyl glycoside catalyzed by cyclodextrin glycosyltransferase (CGTase) |
| |
Authors: | David Svensson Stefan Ulvenlund Patrick Adlercreutz |
| |
Institution: | 1. Department of Biotechnology, Lund University, P.O. Box 124, SE‐221 00 Lund, Sweden;2. Product Development, AstraZeneca R&D Lund, Lund, Sweden |
| |
Abstract: | Alkyl glycosides with long carbohydrate groups are surfactants with attractive properties but they are very difficult to synthesize. Here, a method for extension of the carbohydrate group of commercially available dodecyl‐β‐d ‐maltoside (DDM) is presented. DDM was converted to dodecyl‐β‐d ‐maltooctaoside (DDMO) in a single step by using a CGTase as catalyst and α‐cyclodextrin (α‐CD) as glycosyl donor. The coupling reaction is under kinetic control and the maximum yield depends on the selectivity of the enzyme. The Bacillus macerans CGTase favored the coupling reaction while the Thermoanaerobacter enzyme also catalyzed disproportionation reactions leading to a broader product range. A high ratio α‐CD/DDM favored a high yield of DDMO and yields up to 80% were obtained using the B. macerans enzyme as catalyst. Biotechnol. Bioeng. 2009; 104: 854–861. © 2009 Wiley Periodicals, Inc. |
| |
Keywords: | cyclodextrin glycosyltransferase alkyl glycoside dodecyl α ‐d‐maltooctaoside cyclodextrin transglycosylation coupling reaction |
|
|