Abstract
Alkyl-glucosides and alkyl-polyglucosides are the new-generation biodegradable surfactants with good emulsifying and wetting properties. The α-forms of these glucosides occur in antibiotics and also stimulate nasal absorption of many drugs. In this paper, we report the synthesis of hexyl α-glucoside and α-polyglucosides using cell-bound α-glucosidase activity of a novel strain of Microbacterium paraoxydans. A number of cell-bound glycosyl hydrolase activities were detected in the isolate with the maximum hydrolytic activity of 180 IU g−1 dry wt cells on p-nitrophenyl-α-d-glucopyranoside. In a micro-aqueous system, at a water activity of 0.69, 1.8 g l−1 of hexyl α-glucoside (corresponding to about 25 % yield) was synthesized by whole cells with maltose and hexanol as substrates. The concentration was enhanced to 11 g l−1 (~60 % yield) in a biphasic system at a water content of 60 %. 1H and 13C NMR spectra of the purified compound confirmed the synthesized product to be hexyl-α-d-glucopyranoside, while the presence of hexyl di- and tri-glucosides was confirmed by electrospray ionization mass spectrometry. The cell-driven synthesis makes this an extremely attractive alternative for synthesis of such compounds.
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References
Ahsan F, Arnold J, Meezan E, Pillion DJ (2001) Enhanced bioavailability of calcitonin formulated with alkyl glucosides following nasal and ocular administration in rats. Pharma Res 18:1742–1746
Basso A, Ducret A, Gardossi L, Lortie R (2002) Synthesis of octyl glucopyranoside by almond β-glucosidase adsorbed onto Celite-R640®. Tetrahedron Lett 43:2005–2008
Bergmann S, Rohde M, Hammerschmidt S (2004) Glyceraldehyde-3-phosphate dehydrogenase of Streptococcus pneumoniae is a surface-displayed plasminogen-binding protein. Infect Immun 72:2416–2419
Berthelot K, Delmotte FM (1999) Purification and characterization of an α-glucosidase from Rhizobium sp. (Robinia pseudoacacia L.) strain USDA 4280. Appl Environ Microbiol 65:2907–2911
Bhatia Y, Mishra S, Bisaria VS (2002) Microbial β-glucosidases: cloning, properties and applications. CRC Crit Rev Biotechnol 22:375–407
Das-Bradoo S, Svensson I, Santos J, Plieva F, Mattiasson B, Hatti-Kaul R (2004) Synthesis of alkylgalactosides using whole cells of Bacillus pseudofirmus species as catalysts. J Biotechnol 110:273–286
Ducret A, Trani M, Lortie R (2002) Screening of various glycosidases for the synthesis of octyl glucoside. Biotechnol Bioeng 77:752–757
Fernandez-Arrojo L, Marin D, De Segura AG, Linde D, Alcalde M, Gutierrez-Alonso P, Ghazi I, Plou FJ, Fernandez-Lobato M, Ballesteros A (2007) Transformation of maltose into prebiotic isomaltooligosaccharides by a novel α-glucosidase from Xanthophyllomyces dendrorhous. Process Biochem 42:1530–1536
Gunata Z, Vallier MJ, Sapis JC, Baumes R, Bayonove CL (1994) Enzymatic synthesis of monoterpenyl β-glucosides by various β-glucosidases. Enzyme Microb Technol 16:1055–1058
Hansson T, Adlercreutz P (2002) Enzymatic synthesis of hexyl glycosides from lactose at low water activity and high temperature using hyperthermostable β-glycosidases. Biocatal Biotransform 20:167–178
Hung VS, Hatada Y, Goda S, Lu J, Hidaka Y, Li Z, Akita M, Ohta Y, Watanabe K, Matsui H, Ito S, Horikoshi K (2005) α-Glucosidase from a strain of deep-sea Geobacillus: a potential enzyme for the biosynthesis of complex carbohydrates. Appl Microbiol Biotechnol 68:757–765
Kim YM, Okuyama M, Mori H, Nakai H, Saburi W, Chiba S, Kimura A (2005) Enzymatic synthesis of alkyl α-2-deoxyglucosides by alkyl alcohol resistant α-glucosidase from Aspergillus niger. Tetrahedron-Asymmetry 16:403–409
Kiwada H, Niimura H, Fujisaki Y, Yamada S, Kato Y (1985) Application of synthetic alkyl glucoside vesicles as drug carriers. I. Preparation and physical properties. Chem Pharm Bull 33:753–759
Koto S, Hirooka M, Tashiro T, Sakashita M, Hatachi M, Kono T, Shimizu M, Yoshida N, Kurasawa S, Sakuma N, Sawazaki S, Takeuchi A, Shoya N, Nakamura E (2004) Simple preparation of alkyl and cycloalkyl alpha-glycosides of maltose, cellobiose and lactose. Carbohydr Res 339:2415–2424
Kwon SJ, Jung HC, Pan JG (2007) Transglycosylation in a water-solvent biphasic reaction system with β-galactosidase displayed on the surfaces of Bacillus subtilis spores. Appl Environ Microbiol 73:2251–2256
Ljunger G, Adlercreutz P, Mattiasson B (1994) Enzymatic synthesis of octyl-β-glucoside in octanol at controlled water activity. Enzyme Microb Technol 16:751–755
Luche S, Santoni V, Rabilloud T (2003) Evaluation of non-ionic and zwitterionic detergents as membrane protein solubilizers in two-dimensional electrophoresis. Proteomics 3:249–253
Mladenoska I, Grey CE, Winkelhausen E, Kuzmanova S, Adlercreutz P (2007) Competition between transglycosylation and hydrolysis in almond β-glucosidase-catalyzed conversion of p-nitrophenyl-β-d-glucoside in monophasic water/alcohol mixtures. Biocatal Biotransform 25:382–385
Papanikolaou S (2001) Enzyme-catalyzed synthesis of alkyl-β-glucosides in a water–alcohol two-phase system. Bioresource Technol 77:157–161
Pillion DJ, Ahsan F, Arnold JJ, Balusubramanian BM, Piraner O, Meezan E (2002) Synthetic long chain alkyl maltosides and alkyl sucrose esters as enhancers of nasal insulin absorption. J Pharma Sci 91:1456–1462
Pogorevc M, Stecher H, Faber K (2002) A caveat for the use of logP values for assessment of the biocompatibility of organic solvents. Biotechnol Lett 24:857–860
Rather MY, Mishra S, Chand S (2010) β-Glucosidase catalyzed synthesis of octyl-β-d-glucopyranoside using whole cells of Pichia etchellsii in micro aqueous media. J Biotechnol 150:490–496
Rather MY, Mishra S, Verma V, Chand S (2011) Biotransformation of methyl-β-d-glucopyranoside to higher chain alkyl glucosides by cell bound β-glucosidase of Pichia etchellsii. Bioresource Technol 107: 287–294
Romaniec MPM, Huskisson N, Barker P, Demain AL (1993) Purification and properties of the Clostridium thermocellum bglB gene product expressed in Escherichia coli. Enzyme Microb Technol 15:393–400
Seo SH, Choi KH, Hwang S, Kim J, Park CS, Rho JR, Cha J (2011) Characterization of the catalytic and kinetic properties of a thermostable Thermoplasma acidophilum α-glucosidase and its transglycosylation reaction with arbutin. J Mol Catal B: Enzymatic 72:305–312
Tzortzis G, Goulas AK, Gibson GR (2005) Synthesis of prebiotic galactooligosaccharides using whole cells of a novel strain, Bifidobacterium bifidum NCIMB 41171. Appl Microbiol Biotechnol 68:412–416
Van Rantwijk F, Woudenberg-van Oosterom M, Sheldon RA (1999) Glycosidase-catalyzed synthesis of alkyl glycosides. J Mol Catal B: Enzymatic 6:511–532
Waltermo A, Claesson PM, Simonsson S, Manev E, Johansson I, Bergeron V (1996) Foam and thin-liquid-film studies of alkyl glucoside systems. Langmuir 12:5271–5278
Wehtje E, Kaur J, Adlercreutz P, Chand S, Mattiasson B (1997) Water activity control in enzymatic esterification processes. Enzyme Microb Technol 21:502–510
Yi Q, Sarney DB, Khan JA, Vulfson EN (1998) A novel approach to biotransformations in aqueous-organic two-phase systems: enzymatic synthesis of alkyl β-d-glucosides using microencapsulated β-glucosidase. Biotechnol Bioengg 60:385–390
Acknowledgments
The authors (SM and SC) would like to thank the Defense Research and Development Organization for supporting this project. University Grants Commission (UGC), India, is acknowledged for the award of JRF to SO. Thanks are also extended to Dr. D. Mukherjee (IIIM, Jammu) for the NMR analysis of hexyl glucoside.
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Ojha, S., Mishra, S., Kapoor, S. et al. Synthesis of hexyl α-glucoside and α-polyglucosides by a novel Microbacterium isolate. Appl Microbiol Biotechnol 97, 5293–5301 (2013). https://doi.org/10.1007/s00253-013-4855-4
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DOI: https://doi.org/10.1007/s00253-013-4855-4