Enzymatic O-galactosylation of selected free as well as partially protected ketohexoses

Journal of Carbohydrate Chemistry

Volumn 20, Issue 7-8, 2001, Pages 647-657

  Eder, Brigitte ^a   Lundt, Inge ^b   Stütz, Arnold E ^a   Wrodnigg, Tanja M ^c  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

ASPERGILLUS ORYZAE;

EID: 0035648066     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1081/CAR-100108279     Document Type: Article

References (39)

1. Lichtenthaler, F. W. Towards Improving the Utility of Ketoses as Organic Raw Materials. Carbohydr. Res. 1998, 313, 69-89 and references cited there.
2. Brigl, P.; Schinle, R. Über Benzoyl-und Benzalderivate der Fructose. Ber. Dtsch. Chem. Ges., 1933, 66, 325-330; Schlubach, H. H.; Vorwerk, J. Untersuchungen über L-Sorbose. Ber. Dtsch. Chem. Ges., 1933, 66, 1251-1253; Cramer, F. B.; Pacsu, E. Studies in the Ketone Sugar Series. VIII. The Structure of L-Sorbose Pentaacetate. J. Am. Chem. Soc. 1937, 59, 1467-1469; Zinner, H.; Schneider, U. Mercaptale und Tritylverbindungen der L-Sorbose. Chem. Ber. 1963, 96, 2159-2164; Lichtenthaler, F. W.; Klotz, J.; Flath, F.-J. Acylation and Carbamoylation of D-Fructose: Acyclic, Furanoid and Pyranoid Derivatives and Their Conformational Features. Liebigs Ann., 1995, 2069-2080 and references cited there.
3. Brigl, P.; Schinle, R. Über Benzoyl-und Benzalderivate der Fructose. Ber. Dtsch. Chem. Ges., 1933, 66, 325-330; Schlubach, H. H.; Vorwerk, J. Untersuchungen über L-Sorbose. Ber. Dtsch. Chem. Ges., 1933, 66, 1251-1253; Cramer, F. B.; Pacsu, E. Studies in the Ketone Sugar Series. VIII. The Structure of L-Sorbose Pentaacetate. J. Am. Chem. Soc. 1937, 59, 1467-1469; Zinner, H.; Schneider, U. Mercaptale und Tritylverbindungen der L-Sorbose. Chem. Ber. 1963, 96, 2159-2164; Lichtenthaler, F. W.; Klotz, J.; Flath, F.-J. Acylation and Carbamoylation of D-Fructose: Acyclic, Furanoid and Pyranoid Derivatives and Their Conformational Features. Liebigs Ann., 1995, 2069-2080 and references cited there.
4. Brigl, P.; Schinle, R. Über Benzoyl-und Benzalderivate der Fructose. Ber. Dtsch. Chem. Ges., 1933, 66, 325-330; Schlubach, H. H.; Vorwerk, J. Untersuchungen über L-Sorbose. Ber. Dtsch. Chem. Ges., 1933, 66, 1251-1253; Cramer, F. B.; Pacsu, E. Studies in the Ketone Sugar Series. VIII. The Structure of L-Sorbose Pentaacetate. J. Am. Chem. Soc. 1937, 59, 1467-1469; Zinner, H.; Schneider, U. Mercaptale und Tritylverbindungen der L-Sorbose. Chem. Ber. 1963, 96, 2159-2164; Lichtenthaler, F. W.; Klotz, J.; Flath, F.-J. Acylation and Carbamoylation of D-Fructose: Acyclic, Furanoid and Pyranoid Derivatives and Their Conformational Features. Liebigs Ann., 1995, 2069-2080 and references cited there.
5. Brigl, P.; Schinle, R. Über Benzoyl-und Benzalderivate der Fructose. Ber. Dtsch. Chem. Ges., 1933, 66, 325-330; Schlubach, H. H.; Vorwerk, J. Untersuchungen über L-Sorbose. Ber. Dtsch. Chem. Ges., 1933, 66, 1251-1253; Cramer, F. B.; Pacsu, E. Studies in the Ketone Sugar Series. VIII. The Structure of L-Sorbose Pentaacetate. J. Am. Chem. Soc. 1937, 59, 1467-1469; Zinner, H.; Schneider, U. Mercaptale und Tritylverbindungen der L-Sorbose. Chem. Ber. 1963, 96, 2159-2164; Lichtenthaler, F. W.; Klotz, J.; Flath, F.-J. Acylation and Carbamoylation of D-Fructose: Acyclic, Furanoid and Pyranoid Derivatives and Their Conformational Features. Liebigs Ann., 1995, 2069-2080 and references cited there.
6. Brigl, P.; Schinle, R. Über Benzoyl-und Benzalderivate der Fructose. Ber. Dtsch. Chem. Ges., 1933, 66, 325-330; Schlubach, H. H.; Vorwerk, J. Untersuchungen über L-Sorbose. Ber. Dtsch. Chem. Ges., 1933, 66, 1251-1253; Cramer, F. B.; Pacsu, E. Studies in the Ketone Sugar Series. VIII. The Structure of L-Sorbose Pentaacetate. J. Am. Chem. Soc. 1937, 59, 1467-1469; Zinner, H.; Schneider, U. Mercaptale und Tritylverbindungen der L-Sorbose. Chem. Ber. 1963, 96, 2159-2164; Lichtenthaler, F. W.; Klotz, J.; Flath, F.-J. Acylation and Carbamoylation of D-Fructose: Acyclic, Furanoid and Pyranoid Derivatives and Their Conformational Features. Liebigs Ann., 1995, 2069-2080 and references cited there.
7. Conn, H. O. Lactulose, a Drug in Search for a Modus Operandi. Gastroenterology 1978, 74, 135-138.
8. Schwengers, D. Leucrose, a Ketodisacchride of Industrial Design, In Carbohydrates as Organic Raw Materials; Lichtenthaler, F. W., Ed; VCH Publ.: Weinheim, New York, 1991; 183-195.
9. Siddiqui, I. R. The Sugars of Honey. Adv. Carbohydr. Chem. Biochem. 1970, 25, 285-309; Hudson, C. S. Melezitose and Turanose. Adv. Carbohydr. Chem. 1946, 2, 1-36.
10. Siddiqui, I. R. The Sugars of Honey. Adv. Carbohydr. Chem. Biochem. 1970, 25, 285-309; Hudson, C. S. Melezitose and Turanose. Adv. Carbohydr. Chem. 1946, 2, 1-36.
11. Heyns, K.; Koch, W. Über die Bildung eines Aminozuckers aus D-Fructose und Ammoniak. Z. Naturforsch. 1952, 7, 486-488; Wrodnigg, T. M.; Eder, B. The Amadori and Heyns Rearrangements: Landmarks in the History of Carbohydrate Chemistry or Unrecognized Synthetic Opportunities. Topics Curr. Chem. (Glycoscience) 2001, 215, 115-152.
12. Heyns, K.; Koch, W. Über die Bildung eines Aminozuckers aus D-Fructose und Ammoniak. Z. Naturforsch. 1952, 7, 486-488; Wrodnigg, T. M.; Eder, B. The Amadori and Heyns Rearrangements: Landmarks in the History of Carbohydrate Chemistry or Unrecognized Synthetic Opportunities. Topics Curr. Chem. (Glycoscience) 2001, 215, 115-152.
13. Wrodnigg, T. M.; Stütz, A. E. An Exceptionally Simple Chemical Synthesis of N-Acetyl-D-lactosamine from Lactulose. Angew. Chem., 1999, 111, 854-856; Int. Ed. Engl. 1999, 38, 827-828.
14. Wrodnigg, T. M.; Stütz, A. E. An Exceptionally Simple Chemical Synthesis of N-Acetyl-D-lactosamine from Lactulose. Angew. Chem., 1999, 111, 854-856; Int. Ed. Engl. 1999, 38, 827-828.
15. For a recent review see: Hanisch, F.-G.; Baldus, S. E. The Thomsen-Friedenreich (TF) Antigen: A Critical Review on the Structural, Biosynthetic and Histochemical Aspects of a Pancarcinoma-Associated Antigen. Histol. Histopathol. 1997, 12, 263-281. For recent synthetic approaches see: Gambert, U.; Thiem, J. Chemoenzymatic Preparation of the Thomsen-Friedenreich Antigen Determinant. Carbohydr. Res. 1997, 299, 85-89; Gambert, U.; Thiem, J. Multi-Enzyme System for the Synthesis of the Sialylated Thomsen-Friedenreich Antigen Determinant. Eur. J. Org. Chem. 1999, 1, 107-110.
16. For a recent review see: Hanisch, F.-G.; Baldus, S. E. The Thomsen-Friedenreich (TF) Antigen: A Critical Review on the Structural, Biosynthetic and Histochemical Aspects of a Pancarcinoma-Associated Antigen. Histol. Histopathol. 1997, 12, 263-281. For recent synthetic approaches see: Gambert, U.; Thiem, J. Chemoenzymatic Preparation of the Thomsen-Friedenreich Antigen Determinant. Carbohydr. Res. 1997, 299, 85-89; Gambert, U.; Thiem, J. Multi-Enzyme System for the Synthesis of the Sialylated Thomsen-Friedenreich Antigen Determinant. Eur. J. Org. Chem. 1999, 1, 107-110.
17. For a recent review see: Hanisch, F.-G.; Baldus, S. E. The Thomsen-Friedenreich (TF) Antigen: A Critical Review on the Structural, Biosynthetic and Histochemical Aspects of a Pancarcinoma-Associated Antigen. Histol. Histopathol. 1997, 12, 263-281. For recent synthetic approaches see: Gambert, U.; Thiem, J. Chemoenzymatic Preparation of the Thomsen-Friedenreich Antigen Determinant. Carbohydr. Res. 1997, 299, 85-89; Gambert, U.; Thiem, J. Multi-Enzyme System for the Synthesis of the Sialylated Thomsen-Friedenreich Antigen Determinant. Eur. J. Org. Chem. 1999, 1, 107-110.
18. Kren, V.; Thiem, J. Glycosylation Employing Bio-Systems: from Enzymes to Whole Cells. Chem. Soc. Rev. 1997, 26, 463-473 and references cited there; Fernandez-Mayoralas, A. Synthesis and Modification of Carbohydrates Using Glycosidases and Lipases. Topics Curr. Chem. (Glycoscience) 1997, 186, 1-20 and references cited there.
19. Kren, V.; Thiem, J. Glycosylation Employing Bio-Systems: from Enzymes to Whole Cells. Chem. Soc. Rev. 1997, 26, 463-473 and references cited there; Fernandez-Mayoralas, A. Synthesis and Modification of Carbohydrates Using Glycosidases and Lipases. Topics Curr. Chem. (Glycoscience) 1997, 186, 1-20 and references cited there.
20. Vocadlo, D. J.; Withers, S. G. Glycosidase-Catalysed Oligosaccharide Synthesis. In Carbohydrates in Chemistry and Biology, Ernst B., Hart, G. W., Sinaÿ, P., Eds; Wiley-VCH: Weinheim, 2000; Part 1, Vol. 2, 723-844.
21. Kawamoto M.; Fujii, S.; Suzuki, K. Glucosyltagatose and Its Manufacture. Japanese Patent JP 85-275070 19851209; Chem. Abstr. 1989, 110:133719.
22. Kawamoto M.; Fujii, S.; Suzuki, K. Glucosyltagatose and Its Manufacture. Japanese Patent JP 85-275070 19851209; Chem. Abstr. 1989, 110:133719.
23. th ACS National Meeting, Las Vegas, NV, Sept. 7-11 (1997), American Chemical Society: Washington DC, 1997; Carb-050.
24. Ajisaka, K.; Fujimoto, H.; Nishida, H. Enzymic Synthesis of Disaccharides by the Use of the Reversed Hydrolysis Activity of β-D-Galactosidases. Carbohydr. Res. 1988, 180, 35-42.
25. Fujimoto, H.; Ajisaka, K. Syntheses of α-D-Glucosyl-D-fructoses by Use of a Reversed Hydrolysis Activity of α-Glucosidase. Biotechnol. Lett.1988, 10, 107-112.
26. Fan, J. Q.; Takegawa, K.; Iwahara, S.; Kondo, A.; Kato, I.; Abeygunawardana, C.; Lee, Y. C. Enhanced Transglycosylation Activity of Arthrobacter protophormiae endo-β-N-Acetylglucosaminidase in Media Containing Organic Solvents. J. Biol. Chem. 1995, 270, 17723-17729.
27. Irvine, J.-C.; Garrett, C. S.; Acetone Derivatives of D-Fructose. J. Chem. Soc. 1910, 97, 1277-1284; Barry, C. P.; Honeyman, J. Fructose and Its Derivatives. Adv. Carbohydr. Chem. 1952, 7, 53-98 and references cited there.
28. Irvine, J.-C.; Garrett, C. S.; Acetone Derivatives of D-Fructose. J. Chem. Soc. 1910, 97, 1277-1284; Barry, C. P.; Honeyman, J. Fructose and Its Derivatives. Adv. Carbohydr. Chem. 1952, 7, 53-98 and references cited there.
29. Fischer, E. Ueber die Verbindungen der Zucker mit Alkoholen und Ketonen. Ber. 1895, 28, 1145-1167; Brady, Jr., R. F. Cyclic Acetals of Ketoses. Carbohydr. Res. 1970, 75, 35-40; Kang, J.; Lim, G. J.; Yoon, S. K.; Kim, M. Y. Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose. J. Org. Chem. 1995, 60, 564-577 and references cited there;.
30. Fischer, E. Ueber die Verbindungen der Zucker mit Alkoholen und Ketonen. Ber. 1895, 28, 1145-1167; Brady, Jr., R. F. Cyclic Acetals of Ketoses. Carbohydr. Res. 1970, 75, 35-40; Kang, J.; Lim, G. J.; Yoon, S. K.; Kim, M. Y. Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose. J. Org. Chem. 1995, 60, 564-577 and references cited there;.
31. Fischer, E. Ueber die Verbindungen der Zucker mit Alkoholen und Ketonen. Ber. 1895, 28, 1145-1167; Brady, Jr., R. F. Cyclic Acetals of Ketoses. Carbohydr. Res. 1970, 75, 35-40; Kang, J.; Lim, G. J.; Yoon, S. K.; Kim, M. Y. Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose. J. Org. Chem. 1995, 60, 564-577 and references cited there;.
32. Reichstein, T.; Grüssner, A. Eine Ergiebige Synthese der L-Ascorbinsäure (C-Vitamin). Helv. Chim. Acta 1934, 17, 311-328.
33. Szarek, M. A.; Wu, X.; Szarek, W. A. Synthesis and Evaluation of 1,5,6-Trideoxy-6,6-difluoro-1,5-imino-D-glucitol as a Glucosidase Inhibitor. Carbohydr. Res. 1997, 299, 165-170.
34. Reichstein, T.; Bosshard W. D-Tagatose, Diaceton-D-tagatose und Tagaturonsäure. Helv. Chim. Acta 1934, 17, 755-761; Cubero, I. I.; Lopez-Espinosa M. T. P. Synthetic Application of Partially Protected Fructopyranoses, J. Carbohydr. Chem. 1986, 5, 299-311 and references cited there; Eyrisch, O.; Sinerius, G.; Fessner, W.-D. Facile Enzymic De Novo Synthesis and NMR Spectroscopic Characterization of D-Tagatose 1,6-biphosphate, Carbohydr. Res. 1993, 238, 287-306 and references cited there.
35. Reichstein, T.; Bosshard W. D-Tagatose, Diaceton-D-tagatose und Tagaturonsäure. Helv. Chim. Acta 1934, 17, 755-761; Cubero, I. I.; Lopez-Espinosa M. T. P. Synthetic Application of Partially Protected Fructopyranoses, J. Carbohydr. Chem. 1986, 5, 299-311 and references cited there; Eyrisch, O.; Sinerius, G.; Fessner, W.-D. Facile Enzymic De Novo Synthesis and NMR Spectroscopic Characterization of D-Tagatose 1,6-biphosphate, Carbohydr. Res. 1993, 238, 287-306 and references cited there.
36. Reichstein, T.; Bosshard W. D-Tagatose, Diaceton-D-tagatose und Tagaturonsäure. Helv. Chim. Acta 1934, 17, 755-761; Cubero, I. I.; Lopez-Espinosa M. T. P. Synthetic Application of Partially Protected Fructopyranoses, J. Carbohydr. Chem. 1986, 5, 299-311 and references cited there; Eyrisch, O.; Sinerius, G.; Fessner, W.-D. Facile Enzymic De Novo Synthesis and NMR Spectroscopic Characterization of D-Tagatose 1,6-biphosphate, Carbohydr. Res. 1993, 238, 287-306 and references cited there.
37. Ataie, M.; Buchanan, J. G.; Edgar, A. R.; Kinsman, R. G.; Lyssikatou, M.; Mahon, M. F.; Welsh, P. M. 3,4-Anhydro-1,2-O-isopropylidene-β-D-tagatose and 4,5-Anhydro-1,2-O-isopropylidene-β-D-fructopyranose. Carbohydr. Res. 2000, 323, 36-43.
38. Gizaw, Y.; BeMiller, J. N. Application of a Phase Transfer Reaction to the Synthesis of L-Fructose. Carbohydr. Res. 1995, 266, 81-85; Tokuyama, K.; Honda, E.; Hoki, N. Sorboses. II. Reaction Mechanism of Acetonization of 1,2-O-isopropylidene-α-L-sorbopyranose. J. Org. Chem. 1964, 29, 133-136 and references cited there.
39. Gizaw, Y.; BeMiller, J. N. Application of a Phase Transfer Reaction to the Synthesis of L-Fructose. Carbohydr. Res. 1995, 266, 81-85; Tokuyama, K.; Honda, E.; Hoki, N. Sorboses. II. Reaction Mechanism of Acetonization of 1,2-O-isopropylidene-α-L-sorbopyranose. J. Org. Chem. 1964, 29, 133-136 and references cited there.