D-XYLOSE (D-GLUCOSE) ISOMERASE (EC 5.3.1.5): OBSERVATIONS AND COMMENTS CONCERNING STRUCTURAL REQUIREMENTS OF SUBSTRATES AS WELL AS MECHANISTIC FEATURES

REFERENCES

• Pedersen , S. 1993 . Industrial Aspects of Immobilized Glucose Isomerase . Bioprocess Technol. , 16 : 185 – 208 .
   Google Scholar
• Bhosale , S. H. , Rao , M. B. and Desphande , V. V. 1996 . Molecular and Industrial Aspects of Glucose Isomerase . Microbiol. Rev. , 60 : 280 – 300 . and references cited there
   PubMedGoogle Scholar
• Parker , J. H. 1978 . D-Lyxose as a Substrate for Streptomyces D-Xylose Isomerase . Appl. Environ. Microbiol. , 36 : 969 – 971 .
   Google Scholar
• Kwon , H. J. , Kitada , M. and Horikoshi , K. 1987 . Purification and Properties of D-Xylose Isomerase from Alkalophilic Bacillus No. KX-6 . Agric. Biol. Chem. , 51 : 1983 – 1989 .
   Web of Science ®Google Scholar
• Yamanaka , K. and Takahara , N. 1977 . Purification and Properties of D-Xylose Isomerase from Lactobacillus xylosus . Agric. Biol. Chem. , 41 : 1909 – 1915 .
   Web of Science ®Google Scholar
• Chang , C. , Park , B. C. , Lee , D.-S. and Suh , S. W. 1999 . Crystal Structures of Thermostable Xylose Isomerases from Thermus caldophilus and Thermus thermophilus: Possible Structural Determinants of Thermostability . J. Mol. Biol. , 288 : 623 – 634 .
   Google Scholar
• Liu , S.-Y. , Wiegel , J. and Gherardini , F. C. 1996 . Purification and Cloning of a Thermostable Xylose (Glucose) Isomerase with Acidic pH Optimum from Thermoanaerobacterium Strain JW/SL-YS 489 . J. Bacteriol. , 178 : 5938 – 5945 .
   PubMed Web of Science ®Google Scholar
• Liao , W. X. , Earnest , L. , Kok , S. L. and Jeyaseelan , K. 1995 . Molecular Cloning and Characterization of the Xylose Isomerase Gene from a Thermophilic Bacillus Species . Biochem. Mol. Biol. Int. , 36 : 401 – 410 .
   Google Scholar
• Vielle , C. , Hess , J. M. , Kelly , R. M. and Zeikus , J. G. 1995 . XylA Cloning and Sequencing and Biochemical Characterization of Xylose Isomerase from Thermotoga neapolitana . Appl. Environ. Microbiol. , 61 : 1867 – 1875 .
   Google Scholar
• Quax , W. J. , Mrabet , N. T. , Luiten , R. G.M. , Schuurhuizen , P. S. and Lasters , I. 1991 . Enhancing the Thermostability of Glucose Isomerase by Protein Engineering . Bio./Technol. , 9 : 738 – 742 .
   Google Scholar
• Yamanaka , K. 1968 . Purification, Crystallization and Properties of the D-Xylose Isomerase from Lactobacillus brevis . Biochim. Biophys. Acta , 151 : 670 – 680 .
   PubMed Web of Science ®Google Scholar
• Danno , G. 1971 . D-Glucose-Isomerizing Enzyme from Bacillus coagulans, Strain HN-68. VI. Role of Metal Ions on the Isomerization of D-Glucose and D-Xylose by the Enzyme . Agric. Biol. Chem. , 35 : 997 – 1006 .
   Web of Science ®Google Scholar
• Sanchez , S. and Smiley , K. L. 1975 . Properties of D-Xylose Isomerase from Streptomyces albus . Appl. Microbiol. , 29 : 745 – 750 .
   Google Scholar
• Chmielewski , M. , Chen , M.-S. and Whistler , R. L. 1976 . 6-Thio-β-D-fructopyranose . Carbohydr. Res. , 49 : 479 – 481 .
   Google Scholar
• Card , P. J. , Hitz , W. D. and Ripp , K. G. 1986 . Chemoenzymatic Syntheses of Fructose-Modified Sucroses via Multienzyme Systems. Some Topographical Aspects of the Binding of Sucrose to a Sucrose Carrier Protein . J. Am. Chem. Soc. , 108 : 158 – 161 .
   Google Scholar
• Durrwachter , J. R. , Sweers , H. M. , Nozaki , K. and Wong , C.-H. 1986 . Enzymatic Aldol Reaction/Isomerization as a Route to Unusual Sugars . Tetrahedron Lett. , 27 : 1261 – 1264 .
   Google Scholar
• Durrwachter , J. R. , Drueckhammer , D. G. , Nozaki , K. , Sweers , H. M. and Wong , C.-H. 1986 . Enzymatic Aldol Condensation/Isomerization as a Route to Unusual Sugar Derivatives . J. Am. Chem. Soc. , 108 : 7812 – 7818 .
   PubMed Web of Science ®Google Scholar
• Durrwachter , J. R. and Wong , C.-H. 1988 . Fructose 1,6-Diphosphate Aldolase Catalyzed Stereoselective Synthesis of C-Alkyl and N-Containing Sugars: Thermodynamically Controlled C—C Bond Formations . J. Org. Chem. , 53 : 4175 – 4181 .
   Google Scholar
• Morís-Varas , F. , Qian , X.-H. and Wong , C.-H. 1996 . Enzymatic/Chemical Synthesis and Biological Evaluation of Seven-Membered Imino Cyclitols . J. Am. Chem. Soc. , 118 : 7647 – 7652 .
   Google Scholar
• de Raadt , A. and Stütz , A. E. 1992 . A Simple Convergent Synthesis of the Mannosidase Inhibitor 1-Deoxymannonojirimycin from Sucrose . Tetrahedron Lett. , 33 : 189 – 192 .
   Web of Science ®Google Scholar
• de Raadt , A. , Ebner , M. , Ekhart , C. W. , Fechter , M. , Lechner , A. , Strobl , M. and Stütz , A. E. 1994 . Glucose Isomerase (EC 5.3.1.5) as a Reagent in Carbohydrate Synthesis: Success and Failures with the Isomerisation of Non-natural Derivatives of D-Glucose into the Corresponding 2-Ketoses . Catal. Today , 22 : 549 – 561 .
   Google Scholar
• Andersen , S. M. , Ekhart , C. W. , Lundt , I. and Stütz , A. E. 2000 . Syntheses of Sugar Related Trihydroxyazepanes from Simple Carbohydrates and their Activities as Reversible Glycosidase Inhibitors . Carbohydr. Res. , 326 : 22 – 33 .
   Google Scholar
• Berger , A. , de Raadt , A. , Gradnig , G. , Grasser , M. , Löw , H. and Stütz , A. E. 1992 . A Novel Synthetic Application of Glucose Isomerase: Quantitative Conversion of D-Glucose and L-Idofuranose Derivatives Modified at Position Five into the Corresponding D-Fructo- and L-Sorbopyranoses . Tetrahedron Lett. , 33 : 7125 – 7128 .
   Web of Science ®Google Scholar
• Andersen , S. M. , Ebner , M. , Ekhart , C. W. , Gradnig , G. , Legler , G. , Lundt , I. , Stütz , A. E. , Withers , S. G. and Wrodnigg , T. M. 1997 . Two Isosteric Fluorinated Derivatives of Powerful Glucosidase Inhibitors 1-Deoxynojirimycin and 2,5-Dideoxy-2,5-imino-D-mannitol: Syntheses and Glycosidase Inhibitory Activities of 1,2,5-Trideoxy-2-fluoro-1,5-imino-D-glucitol and of 1,2,5-Trideoxy-1-fluoro-2,5-imino-D-mannitol . Carbohydr. Res. , 301 : 155 – 166 .
   Web of Science ®Google Scholar
• Hadwiger , P. , Mayr , P. , Nidetzky , B. , Stütz , A. E. and Tauss , A. 2000 . Synthesis of 5,6-Dimodified Open-chain D-Fructose Derivatives and Their Properties as Substrates of Bacterial Polyol Dehydrogenase . Tetrahedron: Asymmetry , 11 : 607 – 620 .
   Google Scholar
• Wrodnigg , T. M. , Gaderbauer , W. , Greimel , P. , Häusler , H. , Sprenger , F. K. , Stütz , A. E. , Virgona , C. and Withers , S. G. 2000 . Biologically Active 1-Aminodeoxy Derivatives of the Powerful Glucosidase Inhibitor 2,5-Dideoxy-2,5-imino-D-mannitol . J. Carbohydr. Chem. , 19 : 975 – 990 . Stütz, A. E. Unpublished results
   Web of Science ®Google Scholar
• Ebner , M. and Stütz , A. E. 1998 . Glucose Isomerase Catalysed Isomerisation Reactions of (2R,3R)-Configured Aldofuranoses into the Corresponding Open-chain Ketoses . Carbohydr. Res. , 305 : 331 – 336 .
   Google Scholar
• Fechter , M. H. and Stütz , A. E. 1999 . Synthetic Applications of Glucose Isomerase: Isomerisation of C-5-Modified (2R,3R,4R)-Configured Hexoses into the Corresponding 2-Ketoses . Carbohydr. Res. , 319 : 55 – 62 .
   Google Scholar
• Farber , G. K. , Glasfeld , A. , Tiraby , G. , Ringe , D. and Petsko , G. A. 1989 . Crystallographic Studies on the Mechanism of Xylose Isomerase . Biochemistry , 89 : 7289 – 7297 .
   Google Scholar
• Collyer , C. A. and Blow , D. M. 1990 . Observations of Reaction Intermediates and the Mechanism of Aldose-Ketose Interconversion by D-Xylose Isomerase . Proc. Natl. Acad. Sci. U.S.A. , 87 : 1362 – 1366 .
   PubMed Web of Science ®Google Scholar
• Lee , C. , Bagdasarian , M. , Meng , M. and Zeikus , J. G. 1990 . Catalytic Mechanism of Xylose (Glucose) Isomerase from Clostridium thermosulfurogenes . J. Biol. Chem. , 265 : 19082 – 19090 .
   PubMed Web of Science ®Google Scholar
• Rangarajan , M. and Hartley , B. S. 1992 . Mechanism of D-Fructose Isomerization by Arthrobacter D-Xylose Isomerase . Biochem. J. , 283 : 223 – 233 .
   PubMedGoogle Scholar
• Whitlow , M. , Howard , A. J. , Finzel , B. C. , Poulos , T. L. , Winborne , E. and Gilliland , G. L. 1991 . A Metal-mediated Hydride Shift Mechanism for Xylose Isomerase Based on the 1.6. ANG. Streptomyces rubiginosus Structures with Xylitol and D-Xylose . Proteins: Struct., Funct., Genet. , 9 : 153 – 173 .
   PubMedGoogle Scholar
• Blow , D. M. , Collyer , C. A. , Goldberg , J. D. and Smart , O. S. 1992 . Structure and Mechanism of D-Xylose Isomerase . Faraday Discuss , 93 : 67 – 73 .
   Google Scholar
• Jenkins , J. , Janin , J. , Rey , F. , Chiadmi , M. , van Tilbeurgh , H. , Lasters , I. , De Maeyer , M. , Van Belle , D. , Wodak , S. J. , Lauwereys , M. , Stanssens , P. , Mrabet , N. T. , Snauwaert , J. , Matthyssens , G. and Lambeir , A.-M. 1992 . Protein Engineering of Xylose (Glucose) Isomerase from Actinoplanes missouriensis. 1. Crystallography and Site-Directed Mutagenesis of Metal Binding Sites . Biochemistry , 31 : 5449 – 5458 .
   PubMedGoogle Scholar
• Lambeir , A.-M. , Lauwereys , M. , Stanssens , P. , Mrabet , N. T. , Snauwaert , J. , van Tilbeurgh , H. , Matthyssens , G. , Lasters , I. , De Maeyer , M. , Wodak , S. J. , Jenkins , J. , Chiadmi , M. and Janin , J. 1992 . Protein Engineering of Xylose (Glucose) Isomerase from Actinoplanes missouriensis. 2. Site-Directed Mutagenesis of the Xylose Binding Site . Biochemistry , 31 : 5459 – 5466 .
   PubMedGoogle Scholar
• van Tilbeurgh , H. , Jenkins , J. , Chiadmi , M. , Janin , J. , Wodak , S. J. , Mrabet , N. T. and Lambeir , A.-M. 1992 . Protein Engineering of Xylose (Glucose) Isomerase from Actinoplanes missouriensis. 3. Changing Metal Specificity and the pH Profile by Site-Directed Mutagenesis . Biochemistry , 31 : 5467 – 5471 .
   PubMedGoogle Scholar
• Allen , K. N. , Lavie , A. , Farber , G. K. , Glasfeld , A. , Petsko , G. A. and Ringe , D. 1994 . Isotopic Exchange plus Substrate and Inhibition Kinetics of D-Xylose Isomerase Do Not Support a Proton-Transfer Mechanism . Biochemistry , 33 : 1481 – 1487 .
   PubMedGoogle Scholar
• Whitaker , R. D. , Cho , Y. , Cha , J. , Carrell , H. L. , Glusker , J. P. , Karplus , P. A. and Batt , C. A. 1995 . Probing the Roles of Active Site Residues in D-Xylose Isomerase . J. Biol. Chem. , 270 : 22895 – 22906 .
   PubMed Web of Science ®Google Scholar
• Hu , H. , Liu , H. and Shi , Y. 1997 . The Reaction Pathway of the Isomerization of D-Xylose Catalyzed by the Enzyme D-Xylose Isomerase: A Theoretical Study . Proteins: Struct., Funct., Genet. , 27 : 545 – 555 .
   PubMedGoogle Scholar
• Pastinen , O. , Visuri , K. , Schoemaker , H. E. and Leisola , M. 1999 . Novel Reactions of Xylose Isomerase from Streptomyces rubiginosus . Enzyme Microb. Technol. , 25 : 695 – 700 .
   Google Scholar
• Pastinen , O. , Schoemaker , H. E. and Leisola , M. 1999 . Xylose Isomerase-catalyzed Novel Hexose Epimerization . Biocatal. Biotransform. , 17 : 393 – 400 .
   Web of Science ®Google Scholar
• Bock , K. , Meldal , M. , Meyer , B. and Wiebe , L. 1983 . Isomerization of D-Glucose with Glucose Isomerase. A Mechanistic Study . Acta Chem. Scand. B , 37 : 101 – 108 .
   Google Scholar
• Allen , K. N. , Lavie , A. , Glasfeld , A. , Tanada , T. N. , Gerrity , D. P. , Carlson , S. C. , Farber , G. K. , Petsko , G. A. and Ringe , D. 1994 . Role of the Divalent Metal Ion in Sugar Binding, Ring Opening, and Isomerization by D-Xylose Isomerase: Replacement of a Catalytic Metal by an Amino Acid . Biochemistry , 33 : 1488 – 1494 .
   PubMedGoogle Scholar
• Lavie , A. , Allen , K. N. , Petsko , G. A. and Ringe , D. 1994 . X-Ray Crystallographic Structures of D-Xylose Isomerase-Substrate Complexes Position the Substrate and Provide Evidence for Metal Movement during Catalysis . Biochemistry , 33 : 5469 – 5480 .
   Google Scholar
• Allen , K. N. , Lavie , A. , Petsko , G. A. and Ringe , D. 1995 . Design, Synthesis, and Characterization of a Potent Xylose Isomerase Inhibitor, D-Threonohydroxamic Acid, and High-Resolution X-ray Crystallographic Structure of the Enzyme-Inhibitor Complex . Biochemistry , 34 : 3742 – 3749 .
   Google Scholar
• Fechter , M. H. and Stütz , A. E. in press .
   Google Scholar
• Nifant'ev , E. E. , Rumyantseva , S. A. , Koroteev , M. P. , Cisneros , X. and Kochetkov , N. K. 1982 . 1,2-Cyclophosphites of 3,5,6-Trimethylglucofuranose and 3,5-Dimethylxylofuranose. Zh. . J. Gen. Chem. USSR (Engl. Transl.) , 52 : 819 – 820 . Obshch. Khim. 1982,52,938–939
   Google Scholar
• D-(2-²H)ribose (97%), purchased from Cambridge Isotope Laboratories Andover, MA, , U.S.A.
   Google Scholar
• Seemann , J. E. and Schulz , G. E. 1997 . Structure and Mechanism of L-Fucose Isomerase from Escherichia coli . J. Mol. Biol. , 273 : 256 – 268 .
   Google Scholar
• Vargha , L. 1954 . “ Substitution of Tosyloxy Groups by Acetoxy Groups in Polyhydroxy Compounds ” . In A New Method for Preparing L-Idose Derivatives from D-Glucose. Ber. , Ph.D. Thesis Edited by: Tauss , A. Vol. 87 , 1351 – 1356 . Technische Universität Graz .
   Google Scholar