Abstract
Enzymatically catalysed isomerisation of free sugars is an important and economically viable alternative to chemical means for achieving such transformations. The conversion of D-glucose into D-fructose with D-xylose (D-glucose) isomerase (EC 5.3.1.5) has become a largescale industrial application producing more than ten million tons of fructose syrup annually. Due to the remarkable tolerance of this and related enzymes, for example, L-fucose isomerase (EC 5.3.1.3), for epimers, as well as chemically modified substrate analogues bearing nonnatural features, such as azido or fluoro substituents, a large variety of interesting and novel synthetic applications has become feasible for these remarkably useful and easy-to-handle biocatalysts.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
7 References
Ghosh S, Roseman S (1965) J Biol Chem 240:1531; Corfield AP, Rainey JB, Clamp JR, Wagner SA (1985) Biochim Biophys Acta 840:264 and references cited therein
Ghosh S, Roseman S (1966) Methods Enzymol 8:185
Schomburg D, Salzmann M (eds) (1990) Enzyme handbook, vol 2. Springer, Berlin Heidelberg New York
Goudsmit EM, Neufeld EF (1967) Biochem Biophys Res Commun 26:730; Barber GA, Hebda PA (1982) Methods Enzymol 83:522 and references cited therein
Itoh H, Sato T, Takeuchi T, Khan AR, Izumori K (1995) J Ferment Bioeng 79:184
Itoh H, Sato T, Izumori K (1995) J Ferment Bioeng 80:101
Akabori S, Uehara K, Muramatsu I (1952) Proc Jpn Acad 28:39
Cohen SS (1953) J Biol Chem 201:71
Marshall RO, Kooi ER (1957) Science 125:648
Tsumura N, Sato T (1960) Bull Agric Chem Soc Jpn 24:326
Natake M (1966) Agric Biol Chem 30:887; Natake M (1968) Agric Biol Chem 32:303
Yamanaka K (1963) Agric Biol Chem 27:265
Tsumura N, Sato T (1965) Agric Biol Chem 29:1129
Takasaki Y, Kosugi Y (1969) In: Perlman D (ed) Fermentation advances. Academic Press Inc, New York, p 561
Yamanaka K (1968) Biochem Biophys Acta 151:670
Danno G (1971) Agric Biol Chem 35:997
Sanchez S, Smiley KL (1975) Appl Microbiol 29:745
(a) Parker JH (1978) Appl Environ Microbiol 36:969; (b) Kwon HJ, Kitada M, Horikoshi K (1987) Agric Biol Chem 51:1983; (c) Yamanaka K, Takahara N (1977) Agric Biol Chem 41:1909
(a) Chang C, Park BC, Lee DS, Suh SW (1999) J Mol Biol 288:623; (b) Liu SY, Wiegel J, Gherardini FC (1996) J Bacteriol 178:5938; (c) Liao WX, Earnest L, Kok SL, Jeyaseelan K (1995) Biochem Mol Biol Int 36:401; (d) Vielle C, Hess JM, Kelly RM, Zeikus JG (1995) Appl Environ Microbiol 61:1867; (e) Quax WJ, Mrabet NT, Luiten RGM, Schuurhuizen PS, Lasters I (1991) Bio/Technol 9:738
Suekane M, Tamura M, Tomimura C (1978) Agric Biol Chem 42:909
Yamanaka K (1975) In: Woods W (ed) Methods in enzymology, vol XLI. Academic Press Inc, New York, p 466
Japanese Patent Appl (1965) 27, 525; British Patent 1, 103, 394; (1967) CA 66:84776f
Hagen HH, Pedersen S (1990) In: Gerhartz W (ed) Enzymes in industry. VCH, New York, p 102
Pedersen S (1993) Bioprocess Technol 16:185
Bhosale SH, Rao MB, Desphande VV (1996) Microbiol Rev 60:280 and references cited therein
(a) Rose IA (1970) In: Boyer PD (ed) The enzymes, 3rd edn, vol II. Academic Press, New York, p 290 and references cited therein; (b) Hanson KR, Rose IA (1975) Acc Chem Res 8:1
Blacklow SC, Raines RT, Lim WA, Zamore PD, Knowles JR (1988) Biochemistry 27:1158
Dyson JED, Noltmann EA (1968) J Biol Chem 243:1401
Alworth WL (1975) Stereochemistry and its application in biochemistry. Wiley, New York, p 244
(a) Schray KJ, Rose IA (1971) Biochemistry 10:1058; (b) Feather MS, Desphande V, Lybyer MJ (1970) Biochim Biophys Res Commun 38:859
Bock K, Meldal M, Meyer B, Wiebe L (1983) Acta Chem Scand B 37:101
Makkee M, Kieboom APG, van Bekkum H (1984) Recl Trav Chim Pays-Bas 103:361
Collyer CA, Goldberg JD, Viehmann H, Blow DM, Ramsden NG, Fleet GWJ, Montgomery FJ, Grice P (1992) Biochemistry 31:12211
Carrell HL, Rubin BH, Hurley TJ, Glusker JP (1984) J Biol Chem 259:3230
Hogue-Angeletti RA (1973) J Biol Chem 250:7814
Banner DW, Bloomer AC, Petsko GA, Phillips DC, Pogson CI, Wilson IA, Corran PH, Furth AJ, Milman JD, Offord RE, Priddle JD, Waley SG (1975) Nature 255:609
Stuart DI, Levine M, Muirhead H, Stammers DK (1979) J Mol Biol 134:109
(a) Mavridis IM, Hatada MH, Tulinsky A, Lebioda L (1982) J Mol Biol 152:419; (b) Banner DW, Bloomer AC, Petsko GA, Phillips DC, Wilson IA (1976) Biochem Biophys Res Commun 72:146; (c) Phillips DC, Sternberg MJE, Thornton JM, Wilson IA (1978) J Mol Biol 119:329
Janecek S (1997) Int J Biol Macromol 21:277
Chothia C (1988) Nature 333:598 and references cited therein
Akins J, Brick P, Jones HB, Hirayuma N, Shaw P-C, Blow DM (1986) Biochim Biophys Acta 874:375
Wilhelm M, Hollenberg CP (1985) Nucleic Acids Res 13:5717
Lawlis VB, Dennis MS, Chen EY, Smith DH, Henner DJ (1984) Appl Environ Microbiol 47:15
Saari GC, Kumar AA, Kawasaki GH, Insley MY, O’Hara PJ (1987) J Bacteriol 169:612
Drocourt D, Bejar S, Calmels T, Reynes JP, Tiraby G (1988) Nucleic Acids Res 16:9337
Dauter Z, Dauter M, Hemker J, Witzel H, Wilson KS (1989) FEBS Lett 247:1
Batt CA, Jamieson AC, Vandeyar MA (1990) Proc Natl Acad Sci USA 87:618
Henrick K, Blow DM, Carrell HL, Glusker JP (1987) Protein Eng 1:467
Farber GK, Petsko GA, Ringe D (1987) Protein Eng 1:459
Rey F, Jenkins J, Janin J, Lasters I, Alard P, Claessens M, Matthyssens G, Wodak S (1988) Proteins 4:165
Dauter Z, Terry H, Witzel H, Wilson KS (1990) Acta Crystallogr B 46:833
Carrell HL, Glusker JP, Burger V, Manfre F, Tritsch D, Biellmann J-F (1989) Proc Natl Acad Sci USA 86:4440
Farber GK, Glasfeld A, Tiraby G, Ringe D, Petsko GA (1989) Biochemistry 89:7289
Shiner VJ, Whittaker D (1969) J Am Chem Soc 91:394; Warnhoff EW, Reynolds-Warnhoff P, Wong MYH (1980) J Am Chem Soc 102:5956
Okuyama T, Kimura K, Fueno T (1982) Bull Chem Soc Jpn 55:2285
Collyer CA, Blow DM (1990) Proc Natl Acad Sci USA 87:1362
Lee C, Bagdasarian M, Meng M, Zeikus JG (1990) J Biol Chem 265:19082
Rangarajan M, Hartley BS (1992) Biochem J 283:223
Whitlow M, Howard AJ, Finzel BC, Poulos TL, Winborne E, Gilliland GL (1991) Proteins 9:153
Blow DM, Collyer CA, Goldberg JD, Smart OS (1992) Faraday Discuss 93:67
(a) Jenkins J, Janin J, Rey F, Chiadmi M, van Tilbeurgh H, Lasters I, De Maeyer M, Van Belle D, Wodak SJ, Lauwereys M, Stanssens P, Mrabet NT, Snauwaert J, Matthyssens G, Lambeir A-M (1992) Biochemistry 31:5449; (b) Lambeir A-M, Lauwereys M, Stanssens P, Mrabet NT, Snauwaert J, van Tilbeurgh H, Matthyssens G, Lasters I, De Maeyer M, Wodak SJ, Jenkins J, Chiadmi M, Janin J (1992) ibid 31:5459: (c) van Tilbeurgh H, Jenkins J, Chiadmi M, Janin J, Wodak SJ, Mrabet NT, Lambeir A-M (1992) ibid 31:5467
Collyer CA, Henrick K, Blow DM (1990) J Mol Biol 212:211
Allen KN, Lavie A, Farber GK, Glasfeld A, Petsko GA, Ringe D (1994) Biochemistry 33:1481
de Raadt A, Ebner M, Ekhart CW, Fechter M, Lechner A, Strobl M, Stütz AE (1994) Catal Today 22:549
Allen NK, Lavie A, Glasfeld A, Tanada TN, Gerrity DP, Carlson SC, Farber GK, Petsko GA, Ringe D (1994) Biochemistry 33:1488
Lavie A, Allen KN, Petsko GA, Ringe D (1994) Biochemistry 33:5469
Allen KN, Lavie A, Petsko GA, Ringe D (1995) Biochemistry 34:3742
Meng M, Bagdasarian M, Zeikus JG (1993) Proc Natl Acad Sci USA 88:4015
Whitaker RD, Cho Y, Cha J, Carrell HL, Glusker JP, Karplus PA, Batt CA (1995) J Biol Chem 270:22895
Nagorski RW, Richard JP (1996) J Am Chem Soc 118:7432
Harris DW, Feather MS (1974) J Org Chem 39:724
Hu H, Liu H, Shi Y (1997) Proteins 27:545
Fuxreiter M, Farkas O, Naray-Szabo G (1995) Protein Eng 8:925
Pastinen O, Visuri K, Schoemaker H, Leisola M (1999) Enzyme Microb Techn 25:695
Lehmacher A, Bisswanger H (1990) Biol Chem Hoppe Seyler 371:527
Chmielewski M, Chen M-S, Whistler R (1976) Carbohydr Res 49:479
Card PJ, Hitz WD, Ripp KG (1986) J. Am Chem Soc 108:158
(a) Durrwachter JR, Sweers HM, Nozaki K, Wong C-H (1986) Tetrahedron Lett 27:1261; (b) Durrwachter JR, Drueckhammer DG, Nozaki K, Sweers HM, Wong C-H (1986) J Am Chem Soc 108:7812
(a) Durrwachter JR, Wong C-H (1988) J Org Chem 53:4175; (b) Wong C-H (1991) Microbial aldolases in carbohydrate synthesis. In: Bednarski MD, Simon ES (eds) Enzymes in carbohydrate synthesis. ACS Symposium Series 466, American Chemical Society, Washington, DC, p 23; (c) Morís-Varas F, Qian X-H, Wong C-H (1996) J Am Chem Soc 118:7647
de Raadt A, Stütz AE (1992) Tetrahedron Lett 33:189
Simmonds MSJ, Kite GC, Porter EA (1999) Taxonomic distribution of iminosugars and their biological activities. In: Stütz AE (ed) Iminosugars as glycosidase inhibitors. Wiley-VCH, Weinheim, p 8
Andersen SM, Ekhart CW, Lundt I, Stütz AE (2000) Carbohydr Res 326:22
Berger A, de Raadt A, Gradnig G, Grasser M, Löw H, Stütz AE (1992) Tetrahedron Lett 33:7125
Hadwiger P, Mayr P, Nidetzky B, Stütz AE, Tauss A (2000) Tetrahedron: Asymmetry 11:607
Andersen SM, Ebner M, Ekhart CW, Gradnig G, Legler G, Lundt I, Stütz AE, Withers SG, Wrodnigg T (1997) Carbohydr Res 301:155
Wrodnigg TM, Gaderbauer W, Greimel P, Häusler H, Sprenger FK, Stütz AE, Virgona C, Withers SG (2000) J Carbohydr Chem 19:975
Ebner M, Stütz AE (1998) Carbohydr Res 305:331
Fechter MH, Stütz AE (1999) Carbohydr Res 319:55
Green M, Cohen SS (1955) Bact Proc 127
Green M, Cohen SS (1956) J Biol Chem 219:557
Oliver EJ, Mortlock RP (1971) J Bacteriol 108:293
Izumori K, Yamanaka K (1974) Agr Biol Chem 38:267
Boulter JR, Gielow WO (1973) J Bacteriol 113:687
Seemann JE, Schulz GE (1997) J Mol Biol 273:256
Badía J, Gimenez R, Baldomá L, Barnes E, Fessner W-D, Aguilar J (1991) J Bacteriol 173:5144
(a) Fessner W-D, Badia J, Eyrisch O, Schneider A, Sinerius G (1992) Tetrahedron Lett 33:5231; (b) Fessner W-D, Schneider A, Eyrisch O, Sinerius G, Badía J (1993) Tetrahedron: Asymmetry 4:1183
García-Junceda E, Shen G-J, Alajarín R, Wong C-H (1995) Bioorg Med Chem 3:1349
Alajarín R, García-Junceda E, Wong C-H (1995) J Org Chem 60:4294
Wong C-H, Alajarín R, Morís-Varas F, Blanco O, García-Juneda E (1995) J Org Chem 60:7360
Fessner W-D, Gosse C, Jaeschke G, Eyrisch O (2000) Eur J Org Chem 125
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2001 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Häsler, H., Stütz, A.E. (2001). D-Xylose (D-Glucose) Isomerase and Related Enzymes in Carbohydrate Synthesis. In: Stütz, A.E. (eds) Glycoscience. Topics in Current Chemistry, vol 215. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-44422-X_5
Download citation
DOI: https://doi.org/10.1007/3-540-44422-X_5
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-41383-7
Online ISBN: 978-3-540-44422-0
eBook Packages: Springer Book Archive