A strategy for chemical synthesis of selectively methyl-esterified oligomers of galacturonic acid

Journal of the Chemical Society. Perkin Transactions 1

Volumn , Issue 5, 2001, Pages 543-551

  Clausen, Mads H ^a   Jørgensen, Malene R ^a   Thorsen, Jesper ^a   Madsen, Robert ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; ESTERIFICATION; ESTERS; OXIDATION; POLYSACCHARIDES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

GLYCOSYLATION REACTIONS; OLIGOSACCHARIDES;

OLIGOMERS;

EID: 0035820164     PISSN: 14727781     EISSN: None     Source Type: Journal    
DOI: 10.1039/b006981g     Document Type: Article

References (28)

1. J. Visser and A.G.J. Voragen, Progress in Biotechnology 14 Pectin and Pectinases, Elsevier, Amsterdam, 1996; R.H. Walter, The Chemistry and Technology of Pectin, Academic Press, San Diego, 1991.
2. J. Visser and A.G.J. Voragen, Progress in Biotechnology 14 Pectin and Pectinases, Elsevier, Amsterdam, 1996; R.H. Walter, The Chemistry and Technology of Pectin, Academic Press, San Diego, 1991.
3. For some recent examples, see: R. Körner, G. Limberg, T.M.I.E. Christensen, J. Dalgaard Mikkelsen and P. Roepstorff, Anal. Chem., 1999, 71, 1421; P.J.H. Daas, P.W. Arisz, H.A. Schols, G.A. De Ruiter and A.G.J. Voragen, Anal. Biochem., 1998, 257, 195.
4. For some recent examples, see: R. Körner, G. Limberg, T.M.I.E. Christensen, J. Dalgaard Mikkelsen and P. Roepstorff, Anal. Chem., 1999, 71, 1421; P.J.H. Daas, P.W. Arisz, H.A. Schols, G.A. De Ruiter and A.G.J. Voragen, Anal. Biochem., 1998, 257, 195.
5. T. Sakai, T. Sakamoto, J. Hallaert and E.J. Vandamme, Adv. Appl. Microbiol., 1993, 39, 213.
6. L. Parenicová, J.A.E. Benen, H.C.M. Kester and J. Visser, Biochem. J., 2000, 345, 637; C. Roy, H. Kester, J. Visser, V. Shevchik, N. Hugouvieux-Cotte-Pattat, J. Robert-Baudouy and J. Benen, J. Bacteriol., 1999, 181, 3705; V.E. Shevchik, H.C.M. Kester, J.A.E. Benen, J. Visser, J. Robert-Baudouy and N. Hugouvieux-Cotte-Pattat, J. Bacteriol., 1999, 181, 1652; J.A.E. Benen, H.C.M. Kester and J. Visser, Eur. J. Biochem., 1999, 259, 577; E.M.W. Chen and A.J. Mort, Carbohydr. Polym., 1996, 29, 129.
7. L. Parenicová, J.A.E. Benen, H.C.M. Kester and J. Visser, Biochem. J., 2000, 345, 637; C. Roy, H. Kester, J. Visser, V. Shevchik, N. Hugouvieux-Cotte-Pattat, J. Robert-Baudouy and J. Benen, J. Bacteriol., 1999, 181, 3705; V.E. Shevchik, H.C.M. Kester, J.A.E. Benen, J. Visser, J. Robert-Baudouy and N. Hugouvieux-Cotte-Pattat, J. Bacteriol., 1999, 181, 1652; J.A.E. Benen, H.C.M. Kester and J. Visser, Eur. J. Biochem., 1999, 259, 577; E.M.W. Chen and A.J. Mort, Carbohydr. Polym., 1996, 29, 129.
8. L. Parenicová, J.A.E. Benen, H.C.M. Kester and J. Visser, Biochem. J., 2000, 345, 637; C. Roy, H. Kester, J. Visser, V. Shevchik, N. Hugouvieux-Cotte-Pattat, J. Robert-Baudouy and J. Benen, J. Bacteriol., 1999, 181, 3705; V.E. Shevchik, H.C.M. Kester, J.A.E. Benen, J. Visser, J. Robert-Baudouy and N. Hugouvieux-Cotte-Pattat, J. Bacteriol., 1999, 181, 1652; J.A.E. Benen, H.C.M. Kester and J. Visser, Eur. J. Biochem., 1999, 259, 577; E.M.W. Chen and A.J. Mort, Carbohydr. Polym., 1996, 29, 129.
9. L. Parenicová, J.A.E. Benen, H.C.M. Kester and J. Visser, Biochem. J., 2000, 345, 637; C. Roy, H. Kester, J. Visser, V. Shevchik, N. Hugouvieux-Cotte-Pattat, J. Robert-Baudouy and J. Benen, J. Bacteriol., 1999, 181, 3705; V.E. Shevchik, H.C.M. Kester, J.A.E. Benen, J. Visser, J. Robert-Baudouy and N. Hugouvieux-Cotte-Pattat, J. Bacteriol., 1999, 181, 1652; J.A.E. Benen, H.C.M. Kester and J. Visser, Eur. J. Biochem., 1999, 259, 577; E.M.W. Chen and A.J. Mort, Carbohydr. Polym., 1996, 29, 129.
10. L. Parenicová, J.A.E. Benen, H.C.M. Kester and J. Visser, Biochem. J., 2000, 345, 637; C. Roy, H. Kester, J. Visser, V. Shevchik, N. Hugouvieux-Cotte-Pattat, J. Robert-Baudouy and J. Benen, J. Bacteriol., 1999, 181, 3705; V.E. Shevchik, H.C.M. Kester, J.A.E. Benen, J. Visser, J. Robert-Baudouy and N. Hugouvieux-Cotte-Pattat, J. Bacteriol., 1999, 181, 1652; J.A.E. Benen, H.C.M. Kester and J. Visser, Eur. J. Biochem., 1999, 259, 577; E.M.W. Chen and A.J. Mort, Carbohydr. Polym., 1996, 29, 129.
11. Y. Nakahara and T. Ogawa, Carbohydr. Res., 1990, 205, 147; Y. Nakahara and T. Ogawa, Carbohydr. Res., 1990, 200, 363; Y. Nakahara and T. Ogawa, Carbohydr. Res., 1989, 194, 95.
12. Y. Nakahara and T. Ogawa, Carbohydr. Res., 1990, 205, 147; Y. Nakahara and T. Ogawa, Carbohydr. Res., 1990, 200, 363; Y. Nakahara and T. Ogawa, Carbohydr. Res., 1989, 194, 95.
13. Y. Nakahara and T. Ogawa, Carbohydr. Res., 1990, 205, 147; Y. Nakahara and T. Ogawa, Carbohydr. Res., 1990, 200, 363; Y. Nakahara and T. Ogawa, Carbohydr. Res., 1989, 194, 95.
14. D. Magaud, C. Grandjean, A. Doutheau, D. Anker, V. Shevchik, N. Cotte-Pattat and J. Robert-Baudouy, Carbohydr. Res., 1998, 314, 189; D. Magaud, C. Grandjean, A. Doutheau, D. Anker, V. Shevchik, N. Cotte-Pattat and J. Robert-Baudouy, Tetrahedron Lett., 1997, 38, 241.
15. D. Magaud, C. Grandjean, A. Doutheau, D. Anker, V. Shevchik, N. Cotte-Pattat and J. Robert-Baudouy, Carbohydr. Res., 1998, 314, 189; D. Magaud, C. Grandjean, A. Doutheau, D. Anker, V. Shevchik, N. Cotte-Pattat and J. Robert-Baudouy, Tetrahedron Lett., 1997, 38, 241.
16. H.C.M. Kester, J.A.E. Benen, J. Visser, M.E. Warren, R. Orlando, C. Bergmann, D. Magaud, D. Anker and A. Doutheau, Biochem. J., 2000, 346, 469; L. Parenicová, H.C.M. Kester, J.A.E. Benen and J. Visser, FEBS Lett., 2000, 467, 333; H.C.M. Kester, D. Magaud, C. Roy, D. Anker, A. Doutheau, V. Shevchik, N. Hugouvieux-Cotte-Pattat, J.A.E. Benen and J. Visser, J. Biol. Chem., 1999, 274, 37053.
17. H.C.M. Kester, J.A.E. Benen, J. Visser, M.E. Warren, R. Orlando, C. Bergmann, D. Magaud, D. Anker and A. Doutheau, Biochem. J., 2000, 346, 469; L. Parenicová, H.C.M. Kester, J.A.E. Benen and J. Visser, FEBS Lett., 2000, 467, 333; H.C.M. Kester, D. Magaud, C. Roy, D. Anker, A. Doutheau, V. Shevchik, N. Hugouvieux-Cotte-Pattat, J.A.E. Benen and J. Visser, J. Biol. Chem., 1999, 274, 37053.
18. H.C.M. Kester, J.A.E. Benen, J. Visser, M.E. Warren, R. Orlando, C. Bergmann, D. Magaud, D. Anker and A. Doutheau, Biochem. J., 2000, 346, 469; L. Parenicová, H.C.M. Kester, J.A.E. Benen and J. Visser, FEBS Lett., 2000, 467, 333; H.C.M. Kester, D. Magaud, C. Roy, D. Anker, A. Doutheau, V. Shevchik, N. Hugouvieux-Cotte-Pattat, J.A.E. Benen and J. Visser, J. Biol. Chem., 1999, 274, 37053.
19. B. Fraser-Reid, U.E. Udodong, Z. Wu, H. Ottosson, J.R. Merritt, C.S. Rao, C. Roberts and R. Madsen, Synlett, 1992, 927.
20. V. Ferro, M. Mocerino, R.V. Stick and D.M.G. Tilbrook, Aust. J. Chem., 1988, 41, 813.
21. M. Bertolini and C.P.J. Glaudemans, Carbohydr. Res., 1970, 15, 263.
22. K. Bock, C. Pedersen and H. Pedersen, Adv. Carbohydr. Chem. Biochem., 1984, 42, 193.
23. D.B. Dess and J.C. Martin, J. Am. Chem. Soc., 1991, 113, 7277.
24. A.J. Mancuso, S.-L. Huang and D. Swern, J. Org. Chem., 1978, 43, 2480.
25. G.A. Kraus and B. Roth, J. Org. Chem., 1980, 45, 4825.
26. N. Hashimoto, T. Aoyama and T. Shioiri, Chem. Pharm. Bull., 1981, 29, 1475.
27. U.E. Udodong, C.S. Rao and B. Fraser-Reid, Tetrahedron, 1992, 48, 4713.
28. J.R. Turvey and T.P. Williams, J. Chem. Soc., 1962, 2119.