α-L-fucosidase from paenibacillus thiaminolyticus: Its hydrolytic and transglycosylation abilities

Glycobiology

Volumn 23, Issue 9, 2013, Pages 1052-1065

  Benešová, Eva ^a   Lipovová, Petra ^a   Dvořáková, Hana ^b   Králová, Blanka ^a  

^a Department of Biochemistry and Microbiology ^*  (Czech Republic)

^b INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

L fucosidase; L fucose; Paenibacillus thiaminolyticus; transglycosylation

Indexed keywords

2 PROPANOL; 4 NITROPHENYL ALPHA LEVO FUCOPYRANOSIDE; ALPHA DEXTRO MANNOPYRANOSIDE; ALPHA GALACTOPYRANOSIDE; ALPHA LEVO FUCOPYRANOSIDE; ALPHA LEVO FUCOSIDASE; CHROMOGENIC SUBSTRATE; ESTER DERIVATIVE; GLUCOPYRANOSIDE; N (TERT BUTOXYCARBONYL) LEVO SERINE METHYL ESTER; N (TERT BUTOXYCARBONYL) LEVO THREONINE METHYL ESTER; NITRILOTRIACETATE NICKEL; POLYHISTIDINE TAG; PYRANOSIDE; UNCLASSIFIED DRUG;

AFFINITY CHROMATOGRAPHY; ARTICLE; BACTERIAL CELL; BACTERIAL STRAIN; ENZYME GLYCOSYLATION; ENZYME MECHANISM; ENZYME MODIFICATION; ENZYME SYNTHESIS; ESCHERICHIA COLI; GENE LIBRARY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDE SEQUENCE; PAENIBACILLUS; PAENIBACILLUS THIAMINOLYTICUS; PH; PRIORITY JOURNAL; PROTEIN CLEAVAGE; PROTEIN EXPRESSION; PROTEIN HYDROLYSIS; PROTEIN PURIFICATION; TEMPERATURE; THIN LAYER CHROMATOGRAPHY; TRANSFUCOSYLATION;

L-FUCOSE; PAENIBACILLUS THIAMINOLYTICUS; TRANSGLYCOSYLATION; Α-L-FUCOSIDASE;

ALPHA-L-FUCOSIDASE; FUCOSE; GLYCOSYLATION; HYDROLYSIS; PAENIBACILLUS;

EID: 84880939975     PISSN: 09596658     EISSN: 14602423     Source Type: Journal    
DOI: 10.1093/glycob/cwt041     Document Type: Article

References (63)

1. Ajisaka K, Fujimoto H, Miyasato M. 1998. An α-L-fucosidase from Penicillium multicolor as a candidate enzyme for the synthesis of α(1-3)-linked fucosyl oligosaccharides by transglycosylation. Carbohydr Res. 309: 125-129.
2. Ajisaka K, Shirakabe M. 1992. Regioselective synthesis of α-L-fucosyl-containing disaccharides by use of α-L-fucosidases of various origins. Carbohydr Res. 224: 291-299.
3. Becker DJ, Lowe JB. 2003. Fucose: Biosynthesis and biological function in mammals. Glycobiology. 13(7): 41R-53R.
4. Benešová E, Lipovová P, Dvořá ková H, Králová B. 2010. β-D-Galactosidase from Paenibacillus thiaminolyticus catalyzing transfucosylation reactions. Glycobiology. 20(4): 442-451.
5. Berteau O, Bielicky J, Kilonda A, Machy D, Anson DS, Kenne L. 2004. α-L-Fucosidases: Exoglycosidases with unusual transglycosylation properties. Biochemistry. 43(24): 7881-7891.
6. Bojarová P, Křen V. 2009. Glycosidases: A key to tailored carbohydrates. Trends Biotechnol. 27(4): 199-209.
7. Bradford MM. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 72: 248-254.
8. Brückner J. 1955. Estimation of monosaccharides by the orcinol-sulphuric acid reaction. Biochem J. 60: 200-205.
9. Cantacuzene D, Attal S. 1991. Enzymic synthesis of galactopyranosyl-L- serine derivatives using galactosidases. Carbohydr Res. 211: 327-331.
10. Cantarel BL, Coutinho PM, Rancurel C, Bernard T, Lombard V, Henrissat B. 2009. The Carbohydrate-Active EnZymes database (CAZy): An expert resource for Glycogenomics. Nucleic Acids Res. 37: D233-D238.
11. Cesar LMM, Mendes MA, Tormena CF, Marques MR, de Souza BM, Saidemberg DM, Bittencourt JC, Palma MS. 2005. Isolation and chemical characterization of PwTx-II: A novel alkaloid toxin from the venom of the spider Parawixia bistriata (Araneidae, Araneae). Toxicon. 46: 786-796.
12. Cobucci-Ponzano B, Conte F, Bedini E, Corsaro MM, Parrilli M, Sulzenbacher G, Lipski A, Dal Piaz F, Lepore L, Rossi M, et al. 2009. β-Glycosyl azides as substrates for α-glycosynthases: Preparation of efficient α-L-fucosynthases. Chem Biol. 16: 1097-1108.
13. Copeland RA. 2000. Enzymes: A Practical Introduction to Structure, Mechanism, and Data Analysis. 2nd ed. New York, NY: Wiley-VCH.
14. Cordero OJ, Merino A, de la Cadena MP, Bugía B, Nogueira M, Vinuela JE, Martínez-Zorzano VS, de Carlos A, Rodríguez-Berrocal FJ. 2001. Cell surface human a-L-fucosidase. Eur J Biochem. 268: 3321-3331.
15. Crout DHG, Vic G. 1998. Glycosidases and glycosyl transferases in glycoside and oligosaccharide synthesis. Curr Opin Chem Biol. 2: 98-111.
16. 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: 273-285.
17. D'Auria MV, Minale L, Riccio R. 1993. Polyoxygenated steroids of marine origin. Chem Rev. 93: 1839-1895.
18. Eneyskaya EV, Kulminskaya AA, Kalkkinen N, Nifantiev NE, Arbatskii NP, Saenko AI, Chepurnaya OV, Arutyunyan AV, Shabalin KA, Neustroev KN. 2001. An α-L-fucosidase from Thermus sp. with unusually broad specificity. Glycoconjugate J. 18: 827-834.
19. Flowers HM. 1981. Chemistry and biochemistry of D- and L-fucose. Adv Carbohydr Chem Biochem. 39: 279-345.
20. Henrissat B. 1991. A classification of glycosyl hydrolases based on amino acid sequence similarities. Biochem J. 280: 309-316.
21. Hu Y, Luan H, Zhou K, Ge G, Yang S, Yang L. 2008. Purification and characterization of a novel glycosidase from the chine white jade snail (Achatina fulica) showing transglycosylation activity. Enzyme Microb Technol. 43: 35-42.
22. Koeller KM, Wong CHH. 2000. Synthesis of complex carbohydrates and glycoconjugates: Enzyme-based and programmable one-pot strategies. Chem Rev. 100: 4465-4493.
23. Kon K, Sugi H, Tamai K, Ueda Y, Yamada N. 1990. Synthesis and cytostatic activity of the antitumor antibiotic chartreusin derivatives. J Antibiot. 43 (4): 372-382.
24. Kouptsova OS, Klyachko NL, Levashov AV. 2001. Synthesis of alkyl glycosides catalyzed by β-glycosidase in a system of reverse micelles. Russ J Bioorg Chem. 27(6): 380-384.
25. Křen V, Thiem J. 1997. Glycosylation employing bio-systems: From enzymes to whole cells. Chem Soc Rev. 26: 463-473.
26. Laemmli UK. 1970. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature. 227: 680-685.
27. Leparoux S, Fortun Y, Colas B. 1994. Synthesis of β-galactosyl- (hydroxy amino acid) derivatives using β-galactosidase activity of Achatina achatina digestive juice. Biotechnol Lett. 16(7): 677-682.
28. Lirdprapamongkol K, Svasti J. 2000. Alkyl glucoside synthesis using Thai rosewood β-glucosidase. Biotechnol Lett. 22: 1889-1894.
29. Liu L, Bennett CS, Wong C-H. 2006. Advances in glycoprotein synthesis. Chem Commun. 21: 21-33.
30. Ma B, Simala-Grant JL, Taylor DE. 2006. Fucosylation in prokaryotes and eukaryotes. Glycobiology. 16(12): 158R-184R.
31. Mackenzie LF, Wang Q, Warren RA, Withers SG. 1998. Glycosynthases: Mutant glycosidases for oligosaccharide synthesis. J Am Chem Soc. 120: 5583-5584.
32. Matsumura S, Imai K, Yoshikawa S, Kawada K, Uchibori T. 1990. Surface activities, biodegradability and antimicrobial properties of n-alkyl glucosides, mannosides and galactosides. J Am Oil Chem Soc. 67(12): 996-1001.
33. Mereyala HB, Gurrala SR, Gadikota RR. 1997. Stereoselective synthesis of α-O-fucosylated serine, threonine, tyrosine and saccharides. J Chem Soc Perkin Trans. 1: 3179-3182.
34. Michalski JC, Klein A. 1999. Glycoprotein lysosomal storage disorders: α- and β-mannosidosis, fucosidosis and α-N- acetylgalactosiminidase deficiency. Biochim Biophys Acta. 1455: 69-84.
35. Miyoshi E, Moriwaki K, Nakagawa T. 2008. Biological function of fucosylation in cancer biology. J Biochem. 143: 725-729.
36. Moriwaki K, Miyoshi E. 2010. Fucosylation and gastrointestinal cancer. World J Hepatol. 2(4): 151-161.
37. Nelson DL, Cox MM. 2005. Principles of Biochemistry. 4th ed. New York, NY: W.H. Freeman & Co.
38. Nilsson KGI, Scigelova M. 1994. Synthesis of glycosylated serine and threonine derivatives employing glycosidases. Biotechnol Lett. 16(7): 671-676.
39. Okahata Y, Mori T. 1998. Transglycosylation catalyzed by a lipid-coated β-D-galactosidase in a two-phase aqueous-organic system. J Mol Catal B: Enzymatic. 5: 119-123.
40. Önenli-Mungan N, Özer G, Altunbasak S, Besley G, Yüksel B, Topaloglu AK, Soyupak S. 2004. Fucosidosis with hypothyroidism: A case report. Turk J Pediatr. 46: 170-173.
41. Osanjo G, Dion M, Drone J, Solleux C, Tran V, Rabiller C, Tellier C. 2007. Directed evolution of the α-L-fucosidase from Thermotoga maritima into an α-L-transfucosidase. Biochemistry. 46: 1022-1033.
42. Perugino G, Trincone A, Rossi M, Moracci M. 2004. Oligosaccharide synthesis by glycosynthases. Trends Biotechnol. 22(1): 31-37.
43. Pratt MR, Bertozzi CR. 2005. Synthetic glycopeptides and glycoproteins as tools for biology. Chem Soc Rev. 34: 58-68.
44. Provenzale JM, Barboriak DP, Sims K. 1995. Neuroradiologic findings in fucosidosis, a rare lysosomal storage disease. Am J Neuroradiol. 16: 809-813.
45. Ruiz-Palacios GM, Cervantes LE, Ramos P, Chavez-Munguia B, Newburg DS. 2003. Campylobacter jejuni binds intestinal H(O) antigen (Fucα1, 2Galβ1, 4GlcNAc), and fucosyloligosaccharides of human milk inhibit its binding and infection. J Biol Chem. 278(16): 14112-14120.
46. Sambrook J, Russel DW. 2001. Molecular Cloning: A Laboratory Manual. 3rd ed. New York, NY: Cold Spring Harbor Laboratory Press.
47. Sarney DB, Vulfson EN. 1995. Application of enzymes to the synthesis of surfactants. Trends Biotechnol. 13: 164-172.
48. Seeberger PH, Haase WCH. 2000. Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries. Chem Rev. 100: 4349-4393.
49. Staudacher E, Altmann F, Wilson IBH, März L. 1999. Fucose in N-glycans: From plant to man. Biochim Biophys Acta. 1473: 216-236.
50. Sulzenbacher G, Bignon C, Nishimura T, Tarling CA, Withers SG, Henrissat B, Bourne Y. 2004. Crystal structure of Thermotoga maritima α-L- fucosidase. J Biol Chem. 279(13): 13119-13128.
51. Taggi AE, Meinwald J, Schroeder FC. 2004. A new approach to natural products discovery exemplified by the identification of sulfated nucleosides in spider venom. J Am Chem Soc. 126: 10364-10369.
52. Tarling CA, He S, Sulzenbacher G, Bignon C, Bourne Y, Henrissat B, Withers SG. 2003. Identification of the catalytic nucleophile of the family 29 α-L-fucosidase from Thermotoga maritima through trapping of a covalent glycosyl-enzyme intermediate and mutagenesis. J Biol Chem. 278 (48): 47394-47399.
53. Trincone A, Giordano A. 2006. Glycosyl hydrolases and glycosyltransferases in the synthesis of oligosaccharides. Curr Org Chem. 10: 1163-1193.
54. Vanhooren PT, Vandamme EJ. 1999. L-Fucose: Occurrence, physiological role, chemical, enzymatic and microbial synthesis. J Chem Technol Biotechnol. 74: 479-497.
55. Vermeer HJ, van Dijk CM, Kamerling JP, Vliegenthart JFG. 2001. Fucosylation of linear alcohols: A study of parameters influencing the stereochemistry of glycosylation. Eur J Org Chem. 2001(1): 193-203.
56. Vetere A, Galateo C, Paoletti S. 1997. All-aqueous, regiospecific transglycosylation synthesis of 3-O-α-L-fucopyranosyl-2-acetamido-2-deoxy- D-glucopyranose, a building block for the synthesis of branched oligosaccharides. Biochem Biophys Res Commun. 234: 358-361.
57. von Rybinski W, Hill K. 1998. Alkyl polyglycosides-properties and applications of a new class of surfactants. Angew Chem Int Ed. 37: 1328-1345.
58. Wada J, Honda Y, Nagae M, Kato R, Wakatsuki S, Katayama T, Taniguchi H, Kumagai H, Kitaoka M, Yamamoto K. 2008. 1, 2-α-L-Fucosynthase: A glycosynthase derived from an inverting α-glycosidase with an unusual reaction mechanism. FEBS Lett. 582: 3739-3743.
59. Wang L-X. 2009. Expanding the repertoire of glycosynthases. Chem Biol. 16: 1026-1027.
60. Watt GM, Lowden PAS, Flitsch SL. 1997. Enzyme-catalyzed formation of glycosidic linkages. Curr Opin Struct Biol. 7: 652-660.
61. Wymer N, Toone EJ. 2000. Enzyme-catalyzed synthesis of carbohydrates. Curr Opin Chem Biol. 4: 110-119.
62. Zayni S, Steiner K, Pföstl A, Hofinger A, Kosma P, Schäffer C, Messner P. 2007. The dTDP-4-dehydro-6-deoxyglucose reductase encoding fcd gene is part of the surface layer glycoprotein glycosylation gene cluster of Geobacillus tepidamans GS5-97T. Glycobiology. 17(4): 433-443.
63. Zeng X, Murata T, Usui T. 2003. Glycosidase-catalyzed synthesis of fucosyl diand trisaccharide derivative using α-L-fucosidase from Alcaligenes sp. J Carbohydr Chem. 22(5): 309-316.