Synthesis of hexyl α-glucoside and α-polyglucosides by a novel Microbacterium isolate

Applied Microbiology and Biotechnology

Volumn 97, Issue 12, 2013, Pages 5293-5301

  Ojha, Swati ^a   Mishra, Saroj ^a   Kapoor, Sumeet ^a   Chand, Subhash ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY DELHI   (India)

Author keywords

Glucosidase; Alkyl glucosides and polyglucosides; Microbacterium sp.; Transglycosylation

Indexed keywords

ALKYL-GLUCOSIDES AND POLYGLUCOSIDES; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; GLUCOSIDASE; GLUCOSIDASE ACTIVITY; GLYCOSYL HYDROLASES; HYDROLYTIC ACTIVITIES; MICROBACTERIUM SP; TRANSGLYCOSYLATION;

EMULSIFICATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANTS (BOTANY);

CARBOHYDRATES;

ALPHA GLUCOSIDASE; ALPHA POLYGLUCOSIDE; GLUCOSIDE; HEXANOL; HEXYL ALPHA GLUCOSIDE; HYDROLASE; MALTOSE; UNCLASSIFIED DRUG;

ABSORPTION; ANTIBIOTICS; BIODEGRADATION; CONCENTRATION (COMPOSITION); EMULSION; EXPERIMENTAL STUDY; GLUCOSE; MICROBIAL ACTIVITY; SUBSTRATE;

ARTICLE; BACTERIAL STRAIN; BACTERIUM; BACTERIUM ISOLATE; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; ELECTROSPRAY MASS SPECTROMETRY; ENZYME ACTIVITY; MICROBACTERIUM PARAOXYDANS; NONHUMAN; NUCLEOTIDE SEQUENCE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; WHOLE CELL;

ACTINOMYCETALES; ALPHA-GLUCOSIDASES; CLUSTER ANALYSIS; DNA, BACTERIAL; DNA, RIBOSOMAL; ENZYMES, IMMOBILIZED; GLUCOSIDES; HEXANOLS; MAGNETIC RESONANCE SPECTROSCOPY; MALTOSE; MASS SPECTROMETRY; MOLECULAR SEQUENCE DATA; PHYLOGENY; RNA, RIBOSOMAL, 16S; SEQUENCE ANALYSIS, DNA;

MICROBACTERIUM; MICROBACTERIUM PARAOXYDANS; MICROBACTERIUM SP.;

EID: 84878731998     PISSN: 01757598     EISSN: 14320614     Source Type: Journal    
DOI: 10.1007/s00253-013-4855-4     Document Type: Article

References (30)

1. 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
2. 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
3. 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
4. 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
5. Bhatia Y, Mishra S, Bisaria VS (2002) Microbial β-glucosidases: cloning, properties and applications. CRC Crit Rev Biotechnol 22:375-407
6. 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
7. Ducret A, Trani M, Lortie R (2002) Screening of various glycosidases for the synthesis of octyl glucoside. Biotechnol Bioeng 77:752-757
8. 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
9. 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
10. 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
11. 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
12. 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
13. 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
14. 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
15. 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
16. 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
17. 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
18. 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
19. Papanikolaou S (2001) Enzyme-catalyzed synthesis of alkyl-β- glucosides in a water-alcohol two-phase system. Bioresource Technol 77:157-161
20. 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
21. 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
22. 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
23. 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
24. 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
25. 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
26. 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
27. Van Rantwijk F, Woudenberg-van Oosterom M, Sheldon RA (1999) Glycosidase-catalyzed synthesis of alkyl glycosides. J Mol Catal B: Enzymatic 6:511-532
28. 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
29. Wehtje E, Kaur J, Adlercreutz P, Chand S, Mattiasson B (1997) Water activity control in enzymatic esterification processes. Enzyme Microb Technol 21:502-510
30. 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