Screening of the regioselectivity of acetyl xylan esterase from Bacillus pumilus as a catalyst for the deacetylation of glycoside acetates

Biocatalysis and Biotransformation

Volumn 27, Issue 3, 2009, Pages 226-236

  Moen, Anders Riise ^a   Anthonsen, Thorleif ^a  

^a NORWEGIAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Norway)

Author keywords

Acetyl xylan esterase; Acetylated methyl glycosides; Bacillus pumilus; Regioselective deacetylation

Indexed keywords

ACETYL XYLAN ESTERASE; ACETYLATED METHYL GLYCOSIDES; BACILLUS PUMILUS; D-GLUCOPYRANOSE; DEACETYLATION; GALACTOPYRANOSE; GLUCOPYRANOSE; MANNOPYRANOSE; METHYL GLYCOSIDES; REGIO-SELECTIVE; REGIOSELECTIVE DEACETYLATION; SUGAR ACETATES;

ACETYLATION; BACTERIOLOGY; SUGAR (SUCROSE);

SUGARS;

ACETYLXYLAN ESTERASE; ALPHA DEXTRO GALACTOPYRANOSE; ALPHA DEXTRO GLUCOPYRANOSE; ALPHA DEXTRO MANNOPYRANOSE; BENZYLGLYCOSIDE; CARBOHYDRATE DERIVATIVE; ESTERASE; GLYCOSIDE; METHYLGLYCOSIDE; TETRA O ACETYL ALPHA LEVO GLUCOPYRANOSE; TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSE; TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BACILLUS PUMILUS; BIOCATALYST; BIOTRANSFORMATION; CARBOHYDRATE SYNTHESIS; CONTROLLED STUDY; DEACETYLATION; HYDROLYSIS; NONHUMAN;

BACILLUS PUMILUS; TETRA;

EID: 68049093901     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.1080/10242420902890026     Document Type: Article

References (22)

1. Altaner C, Saake B, Tenkanen M, Eyzaguirre J, Faulds CB, Biely P, Viikari L, Siika-aho M, Puls J. 2003. Regioselective deacetylation of cellulose acetates by acetyl xylan esterases of different CE-families. J Biotechnol 105:95-104.
2. Biely P, Puls J, Schneider H. 1985. Acetyl xylan esterases in fungal cellulolytic systems. FEBS Lett 186:80-84.
3. Caufrier F, Martinou A, Dupont C, Bouriotis V. 2003. Carbohydrate esterase family 4 enzymes: Substrate specificity. Carbohydr Res 338:687-692.
4. Degrassi G, Okeke BC, Bruschi CV, Venturi V. 1998. Purification and characterization of an acetyl xylan esterase from Bacillus pumilus Appl Environ Microbiol 64:789-792.
5. Degrassi G, Kojic M, Ljubijankic G, Venturi V. 2000. The acetyl xylan esterase of Bacillus pumilus belongs to a family of esterases with broad substrate specificity. Microbiology 146:1585-1591.
6. Fischer E. 1920. Wanderung von acyl bei den glyceriden. Chem Ber 53:1621-1633.
7. Hanessian S, Kagotani M. 1990. Novel methods for the preparation of partially acetylated carbohydrates. Carbohydr Res 202:67-79.
8. Horrobin T, Tran CH, Crout D. 1998. Esterase-catalyzed regioselective 6-deacylation of hexopyranose per-acetates, acid-catalyzed rearrangement to the 4-deprotected products and conversions of these into hexose 4- and 6-sulfates. J Chem Soc, Perkin Trans 1:1069-1080.
9. Ikeda I, Klibanov AM. 1993. Lipase-catalyzed acylation of sugars solubilized in hydrophobic solvents by complexation. Biotechnol Bioeng 42:788-791.
10. Jansson PE, Kenne L, Schweda E. 1987. Nuclear magnetic resonance and conformational studies on monoacetylated methyl D-gluco- and D-galactopyranosides. J Chem Soc, Perkin Trans 1:377-383.
11. Kadereit D, Waldmann H. 2001. Enzymatic protecting group techniques. Chem Rev 101:3367-3396.
12. Krastanova I, Guarnacca C, Zahariev S, Degrassi G, Lamba D. 2005. Heterologous expression, purification, crystallization, X-ray analysis and phasing of the acetyl xylan esterase from Bacillus pumilus. Biochim Biophys Acta 1748:222-230.
13. La Ferla B. 2002. Lipases as useful tools for the stereo- and regioselective protection and deprotection of carbohydrates. Monatsh Chem 133:351-368.
14. Moriyoshi K, Yamanaka H, Ohmoto T, Ohe T, Sakai K. 2005. Mode of action on deacetylation of acetylated methyl glycoside by cellulose acetate esterase from Neisseria sicca SB. Biosci Biotechnol Biochem 69:1292-1299.
15. Morley KL, Chauve G, Kazlauskas R, Dupont C, Shareck F, Marchessault RH. 2006. Acetyl xylan esterase-catalyzed deacetylation of chitin and chitosan. Carbohydr Polym 63: 310-315.
16. Oscarson S. 2006. Protective group strategies. In: Levy DE, Fügedi P, editors. The organic chemistry of sugars. London: Taylor & Francis Group. p 53-87.
17. Sjursnes BJ, Anthonsen T. 1994. Acyl migration in 1,2-dibutyrin, dependence on solvent and water activity. Biocatalysis 9: 285-297.
18. Sweers HM, Wong C-H. 1986. Enzyme-catalyzed regioselective deacylation of protected sugars in carbohydrate synthesis. J Am Chem Soc 108:6421-6422.
19. Therisod M, Klibanov AM. 1987. Regioselective acylation of secondary hydroxyl groups in sugars catalyzed by lipases in organic solvents. J Am Chem Soc 109:3977-3981.
20. Thiem J. 1995. Applications of enzymes in synthetic carbohydrate chemistry. FEMS Microbiol Rev 16:193-211.
21. Vazquez JT, Wiesler WT, Nakanishi K. 1988. Circular dichroism spectra of bichromophorically derivatized methyl-D-galactopyranosides, calculable by pairwise additivity, provide a basis for novel microanalysis of oligosaccharides. Carbohydr Res 176:175-194.
22. Vincent F, Charnock SJ, Verschueren KHG, Turkenburg JP, Scott DJ, Offen WA, Roberts S, Pell G, Gilbert HJ, Davies GJ, Brannigan JA. 2003. Multifunctional xylooligosaccharide/cephalosporin C deacetylase revealed by the hexameric structure of the Bacillus subtilis enzyme at 1.9 ANG. resolution. J Mol Biol 330:593-606.