A novel three-enzyme reaction cycle for the synthesis of N-acetyllactosamine with in situ regeneration of uridine 5′-diphosphate glucose and uridine 5′-diphosphate galactose

Journal of the American Chemical Society

Volumn 118, Issue 8, 1996, Pages 1836-1840

  Zervosen, Astrid ^a   Elling, Lothar ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

GALACTOSYLTRANSFERASE; GLUCOSAMINE DERIVATIVE; N ACETYLLACTOSAMINE; SUCROSE SYNTHASE; UNCLASSIFIED DRUG; URIDINE DIPHOSPHATE GALACTOSE; URIDINE DIPHOSPHATE GLUCOSE; URIDINE DIPHOSPHATE GLUCOSE 4 EPIMERASE;

ARTICLE; CARBOHYDRATE SYNTHESIS; ENZYME ACTIVITY; REACTION ANALYSIS;

EID: 0029878026     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953495e     Document Type: Article

References (51)

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14. Chemical synthesis: (a) Kochetkov, N. K.; Shibaev, V. N. In Advances in carbohydrate chemistry and biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1973; Vol. 28, pp 307-399. (b) Ichikawa, Y.; Sim, M. M.; Wong, C.-H. J. Org. Chem. 1992, 57, 2943-2946. (c) Sim, M. M., Kondo, H.; Wong, C. H. J. Am. Chem. Soc. 1993, 115, 2260-2267. (d) Schmidt, R. R; Wegmann, B.; Jung, K.-H. Liebigs Ann. Chem. 1991, 2, 121-124. (e) Gokhale, U. B.; Hindsgaul. O.; Palcic, M. M. Can. J. Chem. 1990, 68, 1063-1071. (f) Klaffke, W. Carbohydr. Res. 1995, 266, 285-292. (g) Arlt, M.; Hindsgaul, O. J. Org. Chem. 1995, 60, 14-15. Enzymatic synthesis: (h) Toone, E. J.; Whitesides, G. M. Am. Chem. Soc. Symp. Ser. 1991, 466, 1-22. (i) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. In Tetrahedron Organic Chemistry Series, Vol. 12; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science: Oxford, U. K., 1994; pp252-311. (j) Heidlas, J. E.: Lees, W. J.; Whitesides, G M. J. Org. Chem. 1992, 57, 152-157. (k) Heidlas, J. E.; Lees, W. J.; Pale, P.; Whitesides, G. M. J. Org. Chem. 1992, 57, 146-151. (l) Simon, E. S.; Grabowski, S.; Whitesides, G. M. J. Org. Chem. 1990, 55, 1834-1841. (m) Toone, E. J.; Simon, E. S.; Whitesides, G. M. J. Org. Chem. 1991, 56, 5603-5606. (n) Shames, S. L.; Simon, E. S.; Christopher, C. W.; Schmid, W.; Whitesides, G M.; Yang. L.-L. Glycobtology 1991, 1, 187-191. (o) Shen, G.-J.; Liu, J. L.-C.; Wong, C.-H. Biocatalysis 1992, 6, 31-42.
15. Chemical synthesis: (a) Kochetkov, N. K.; Shibaev, V. N. In Advances in carbohydrate chemistry and biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1973; Vol. 28, pp 307-399. (b) Ichikawa, Y.; Sim, M. M.; Wong, C.-H. J. Org. Chem. 1992, 57, 2943-2946. (c) Sim, M. M., Kondo, H.; Wong, C. H. J. Am. Chem. Soc. 1993, 115, 2260-2267. (d) Schmidt, R. R; Wegmann, B.; Jung, K.-H. Liebigs Ann. Chem. 1991, 2, 121-124. (e) Gokhale, U. B.; Hindsgaul. O.; Palcic, M. M. Can. J. Chem. 1990, 68, 1063-1071. (f) Klaffke, W. Carbohydr. Res. 1995, 266, 285-292. (g) Arlt, M.; Hindsgaul, O. J. Org. Chem. 1995, 60, 14-15. Enzymatic synthesis: (h) Toone, E. J.; Whitesides, G. M. Am. Chem. Soc. Symp. Ser. 1991, 466, 1-22. (i) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. In Tetrahedron Organic Chemistry Series, Vol. 12; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science: Oxford, U. K., 1994; pp252-311. (j) Heidlas, J. E.: Lees, W. J.; Whitesides, G M. J. Org. Chem. 1992, 57, 152-157. (k) Heidlas, J. E.; Lees, W. J.; Pale, P.; Whitesides, G. M. J. Org. Chem. 1992, 57, 146-151. (l) Simon, E. S.; Grabowski, S.; Whitesides, G. M. J. Org. Chem. 1990, 55, 1834-1841. (m) Toone, E. J.; Simon, E. S.; Whitesides, G. M. J. Org. Chem. 1991, 56, 5603-5606. (n) Shames, S. L.; Simon, E. S.; Christopher, C. W.; Schmid, W.; Whitesides, G M.; Yang. L.-L. Glycobtology 1991, 1, 187-191. (o) Shen, G.-J.; Liu, J. L.-C.; Wong, C.-H. Biocatalysis 1992, 6, 31-42.
16. Chemical synthesis: (a) Kochetkov, N. K.; Shibaev, V. N. In Advances in carbohydrate chemistry and biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1973; Vol. 28, pp 307-399. (b) Ichikawa, Y.; Sim, M. M.; Wong, C.-H. J. Org. Chem. 1992, 57, 2943-2946. (c) Sim, M. M., Kondo, H.; Wong, C. H. J. Am. Chem. Soc. 1993, 115, 2260-2267. (d) Schmidt, R. R; Wegmann, B.; Jung, K.-H. Liebigs Ann. Chem. 1991, 2, 121-124. (e) Gokhale, U. B.; Hindsgaul. O.; Palcic, M. M. Can. J. Chem. 1990, 68, 1063-1071. (f) Klaffke, W. Carbohydr. Res. 1995, 266, 285-292. (g) Arlt, M.; Hindsgaul, O. J. Org. Chem. 1995, 60, 14-15. Enzymatic synthesis: (h) Toone, E. J.; Whitesides, G. M. Am. Chem. Soc. Symp. Ser. 1991, 466, 1-22. (i) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. In Tetrahedron Organic Chemistry Series, Vol. 12; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science: Oxford, U. K., 1994; pp252-311. (j) Heidlas, J. E.: Lees, W. J.; Whitesides, G M. J. Org. Chem. 1992, 57, 152-157. (k) Heidlas, J. E.; Lees, W. J.; Pale, P.; Whitesides, G. M. J. Org. Chem. 1992, 57, 146-151. (l) Simon, E. S.; Grabowski, S.; Whitesides, G. M. J. Org. Chem. 1990, 55, 1834-1841. (m) Toone, E. J.; Simon, E. S.; Whitesides, G. M. J. Org. Chem. 1991, 56, 5603-5606. (n) Shames, S. L.; Simon, E. S.; Christopher, C. W.; Schmid, W.; Whitesides, G M.; Yang. L.-L. Glycobtology 1991, 1, 187-191. (o) Shen, G.-J.; Liu, J. L.-C.; Wong, C.-H. Biocatalysis 1992, 6, 31-42.
17. Chemical synthesis: (a) Kochetkov, N. K.; Shibaev, V. N. In Advances in carbohydrate chemistry and biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1973; Vol. 28, pp 307-399. (b) Ichikawa, Y.; Sim, M. M.; Wong, C.-H. J. Org. Chem. 1992, 57, 2943-2946. (c) Sim, M. M., Kondo, H.; Wong, C. H. J. Am. Chem. Soc. 1993, 115, 2260-2267. (d) Schmidt, R. R; Wegmann, B.; Jung, K.-H. Liebigs Ann. Chem. 1991, 2, 121-124. (e) Gokhale, U. B.; Hindsgaul. O.; Palcic, M. M. Can. J. Chem. 1990, 68, 1063-1071. (f) Klaffke, W. Carbohydr. Res. 1995, 266, 285-292. (g) Arlt, M.; Hindsgaul, O. J. Org. Chem. 1995, 60, 14-15. Enzymatic synthesis: (h) Toone, E. J.; Whitesides, G. M. Am. Chem. Soc. Symp. Ser. 1991, 466, 1-22. (i) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. In Tetrahedron Organic Chemistry Series, Vol. 12; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science: Oxford, U. K., 1994; pp252-311. (j) Heidlas, J. E.: Lees, W. J.; Whitesides, G M. J. Org. Chem. 1992, 57, 152-157. (k) Heidlas, J. E.; Lees, W. J.; Pale, P.; Whitesides, G. M. J. Org. Chem. 1992, 57, 146-151. (l) Simon, E. S.; Grabowski, S.; Whitesides, G. M. J. Org. Chem. 1990, 55, 1834-1841. (m) Toone, E. J.; Simon, E. S.; Whitesides, G. M. J. Org. Chem. 1991, 56, 5603-5606. (n) Shames, S. L.; Simon, E. S.; Christopher, C. W.; Schmid, W.; Whitesides, G M.; Yang. L.-L. Glycobtology 1991, 1, 187-191. (o) Shen, G.-J.; Liu, J. L.-C.; Wong, C.-H. Biocatalysis 1992, 6, 31-42.
18. Chemical synthesis: (a) Kochetkov, N. K.; Shibaev, V. N. In Advances in carbohydrate chemistry and biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1973; Vol. 28, pp 307-399. (b) Ichikawa, Y.; Sim, M. M.; Wong, C.-H. J. Org. Chem. 1992, 57, 2943-2946. (c) Sim, M. M., Kondo, H.; Wong, C. H. J. Am. Chem. Soc. 1993, 115, 2260-2267. (d) Schmidt, R. R; Wegmann, B.; Jung, K.-H. Liebigs Ann. Chem. 1991, 2, 121-124. (e) Gokhale, U. B.; Hindsgaul. O.; Palcic, M. M. Can. J. Chem. 1990, 68, 1063-1071. (f) Klaffke, W. Carbohydr. Res. 1995, 266, 285-292. (g) Arlt, M.; Hindsgaul, O. J. Org. Chem. 1995, 60, 14-15. Enzymatic synthesis: (h) Toone, E. J.; Whitesides, G. M. Am. Chem. Soc. Symp. Ser. 1991, 466, 1-22. (i) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. In Tetrahedron Organic Chemistry Series, Vol. 12; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science: Oxford, U. K., 1994; pp252-311. (j) Heidlas, J. E.: Lees, W. J.; Whitesides, G M. J. Org. Chem. 1992, 57, 152-157. (k) Heidlas, J. E.; Lees, W. J.; Pale, P.; Whitesides, G. M. J. Org. Chem. 1992, 57, 146-151. (l) Simon, E. S.; Grabowski, S.; Whitesides, G. M. J. Org. Chem. 1990, 55, 1834-1841. (m) Toone, E. J.; Simon, E. S.; Whitesides, G. M. J. Org. Chem. 1991, 56, 5603-5606. (n) Shames, S. L.; Simon, E. S.; Christopher, C. W.; Schmid, W.; Whitesides, G M.; Yang. L.-L. Glycobtology 1991, 1, 187-191. (o) Shen, G.-J.; Liu, J. L.-C.; Wong, C.-H. Biocatalysis 1992, 6, 31-42.
19. Chemical synthesis: (a) Kochetkov, N. K.; Shibaev, V. N. In Advances in carbohydrate chemistry and biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1973; Vol. 28, pp 307-399. (b) Ichikawa, Y.; Sim, M. M.; Wong, C.-H. J. Org. Chem. 1992, 57, 2943-2946. (c) Sim, M. M., Kondo, H.; Wong, C. H. J. Am. Chem. Soc. 1993, 115, 2260-2267. (d) Schmidt, R. R; Wegmann, B.; Jung, K.-H. Liebigs Ann. Chem. 1991, 2, 121-124. (e) Gokhale, U. B.; Hindsgaul. O.; Palcic, M. M. Can. J. Chem. 1990, 68, 1063-1071. (f) Klaffke, W. Carbohydr. Res. 1995, 266, 285-292. (g) Arlt, M.; Hindsgaul, O. J. Org. Chem. 1995, 60, 14-15. Enzymatic synthesis: (h) Toone, E. J.; Whitesides, G. M. Am. Chem. Soc. Symp. Ser. 1991, 466, 1-22. (i) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. In Tetrahedron Organic Chemistry Series, Vol. 12; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science: Oxford, U. K., 1994; pp252-311. (j) Heidlas, J. E.: Lees, W. J.; Whitesides, G M. J. Org. Chem. 1992, 57, 152-157. (k) Heidlas, J. E.; Lees, W. J.; Pale, P.; Whitesides, G. M. J. Org. Chem. 1992, 57, 146-151. (l) Simon, E. S.; Grabowski, S.; Whitesides, G. M. J. Org. Chem. 1990, 55, 1834-1841. (m) Toone, E. J.; Simon, E. S.; Whitesides, G. M. J. Org. Chem. 1991, 56, 5603-5606. (n) Shames, S. L.; Simon, E. S.; Christopher, C. W.; Schmid, W.; Whitesides, G M.; Yang. L.-L. Glycobtology 1991, 1, 187-191. (o) Shen, G.-J.; Liu, J. L.-C.; Wong, C.-H. Biocatalysis 1992, 6, 31-42.
20. Chemical synthesis: (a) Kochetkov, N. K.; Shibaev, V. N. In Advances in carbohydrate chemistry and biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1973; Vol. 28, pp 307-399. (b) Ichikawa, Y.; Sim, M. M.; Wong, C.-H. J. Org. Chem. 1992, 57, 2943-2946. (c) Sim, M. M., Kondo, H.; Wong, C. H. J. Am. Chem. Soc. 1993, 115, 2260-2267. (d) Schmidt, R. R; Wegmann, B.; Jung, K.-H. Liebigs Ann. Chem. 1991, 2, 121-124. (e) Gokhale, U. B.; Hindsgaul. O.; Palcic, M. M. Can. J. Chem. 1990, 68, 1063-1071. (f) Klaffke, W. Carbohydr. Res. 1995, 266, 285-292. (g) Arlt, M.; Hindsgaul, O. J. Org. Chem. 1995, 60, 14-15. Enzymatic synthesis: (h) Toone, E. J.; Whitesides, G. M. Am. Chem. Soc. Symp. Ser. 1991, 466, 1-22. (i) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. In Tetrahedron Organic Chemistry Series, Vol. 12; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science: Oxford, U. K., 1994; pp252-311. (j) Heidlas, J. E.: Lees, W. J.; Whitesides, G M. J. Org. Chem. 1992, 57, 152-157. (k) Heidlas, J. E.; Lees, W. J.; Pale, P.; Whitesides, G. M. J. Org. Chem. 1992, 57, 146-151. (l) Simon, E. S.; Grabowski, S.; Whitesides, G. M. J. Org. Chem. 1990, 55, 1834-1841. (m) Toone, E. J.; Simon, E. S.; Whitesides, G. M. J. Org. Chem. 1991, 56, 5603-5606. (n) Shames, S. L.; Simon, E. S.; Christopher, C. W.; Schmid, W.; Whitesides, G M.; Yang. L.-L. Glycobtology 1991, 1, 187-191. (o) Shen, G.-J.; Liu, J. L.-C.; Wong, C.-H. Biocatalysis 1992, 6, 31-42.
21. Chemical synthesis: (a) Kochetkov, N. K.; Shibaev, V. N. In Advances in carbohydrate chemistry and biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1973; Vol. 28, pp 307-399. (b) Ichikawa, Y.; Sim, M. M.; Wong, C.-H. J. Org. Chem. 1992, 57, 2943-2946. (c) Sim, M. M., Kondo, H.; Wong, C. H. J. Am. Chem. Soc. 1993, 115, 2260-2267. (d) Schmidt, R. R; Wegmann, B.; Jung, K.-H. Liebigs Ann. Chem. 1991, 2, 121-124. (e) Gokhale, U. B.; Hindsgaul. O.; Palcic, M. M. Can. J. Chem. 1990, 68, 1063-1071. (f) Klaffke, W. Carbohydr. Res. 1995, 266, 285-292. (g) Arlt, M.; Hindsgaul, O. J. Org. Chem. 1995, 60, 14-15. Enzymatic synthesis: (h) Toone, E. J.; Whitesides, G. M. Am. Chem. Soc. Symp. Ser. 1991, 466, 1-22. (i) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. In Tetrahedron Organic Chemistry Series, Vol. 12; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science: Oxford, U. K., 1994; pp252-311. (j) Heidlas, J. E.: Lees, W. J.; Whitesides, G M. J. Org. Chem. 1992, 57, 152-157. (k) Heidlas, J. E.; Lees, W. J.; Pale, P.; Whitesides, G. M. J. Org. Chem. 1992, 57, 146-151. (l) Simon, E. S.; Grabowski, S.; Whitesides, G. M. J. Org. Chem. 1990, 55, 1834-1841. (m) Toone, E. J.; Simon, E. S.; Whitesides, G. M. J. Org. Chem. 1991, 56, 5603-5606. (n) Shames, S. L.; Simon, E. S.; Christopher, C. W.; Schmid, W.; Whitesides, G M.; Yang. L.-L. Glycobtology 1991, 1, 187-191. (o) Shen, G.-J.; Liu, J. L.-C.; Wong, C.-H. Biocatalysis 1992, 6, 31-42.
22. Chemical synthesis: (a) Kochetkov, N. K.; Shibaev, V. N. In Advances in carbohydrate chemistry and biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1973; Vol. 28, pp 307-399. (b) Ichikawa, Y.; Sim, M. M.; Wong, C.-H. J. Org. Chem. 1992, 57, 2943-2946. (c) Sim, M. M., Kondo, H.; Wong, C. H. J. Am. Chem. Soc. 1993, 115, 2260-2267. (d) Schmidt, R. R; Wegmann, B.; Jung, K.-H. Liebigs Ann. Chem. 1991, 2, 121-124. (e) Gokhale, U. B.; Hindsgaul. O.; Palcic, M. M. Can. J. Chem. 1990, 68, 1063-1071. (f) Klaffke, W. Carbohydr. Res. 1995, 266, 285-292. (g) Arlt, M.; Hindsgaul, O. J. Org. Chem. 1995, 60, 14-15. Enzymatic synthesis: (h) Toone, E. J.; Whitesides, G. M. Am. Chem. Soc. Symp. Ser. 1991, 466, 1-22. (i) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. In Tetrahedron Organic Chemistry Series, Vol. 12; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science: Oxford, U. K., 1994; pp252-311. (j) Heidlas, J. E.: Lees, W. J.; Whitesides, G M. J. Org. Chem. 1992, 57, 152-157. (k) Heidlas, J. E.; Lees, W. J.; Pale, P.; Whitesides, G. M. J. Org. Chem. 1992, 57, 146-151. (l) Simon, E. S.; Grabowski, S.; Whitesides, G. M. J. Org. Chem. 1990, 55, 1834-1841. (m) Toone, E. J.; Simon, E. S.; Whitesides, G. M. J. Org. Chem. 1991, 56, 5603-5606. (n) Shames, S. L.; Simon, E. S.; Christopher, C. W.; Schmid, W.; Whitesides, G M.; Yang. L.-L. Glycobtology 1991, 1, 187-191. (o) Shen, G.-J.; Liu, J. L.-C.; Wong, C.-H. Biocatalysis 1992, 6, 31-42.
23. Chemical synthesis: (a) Kochetkov, N. K.; Shibaev, V. N. In Advances in carbohydrate chemistry and biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1973; Vol. 28, pp 307-399. (b) Ichikawa, Y.; Sim, M. M.; Wong, C.-H. J. Org. Chem. 1992, 57, 2943-2946. (c) Sim, M. M., Kondo, H.; Wong, C. H. J. Am. Chem. Soc. 1993, 115, 2260-2267. (d) Schmidt, R. R; Wegmann, B.; Jung, K.-H. Liebigs Ann. Chem. 1991, 2, 121-124. (e) Gokhale, U. B.; Hindsgaul. O.; Palcic, M. M. Can. J. Chem. 1990, 68, 1063-1071. (f) Klaffke, W. Carbohydr. Res. 1995, 266, 285-292. (g) Arlt, M.; Hindsgaul, O. J. Org. Chem. 1995, 60, 14-15. Enzymatic synthesis: (h) Toone, E. J.; Whitesides, G. M. Am. Chem. Soc. Symp. Ser. 1991, 466, 1-22. (i) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. In Tetrahedron Organic Chemistry Series, Vol. 12; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science: Oxford, U. K., 1994; pp252-311. (j) Heidlas, J. E.: Lees, W. J.; Whitesides, G M. J. Org. Chem. 1992, 57, 152-157. (k) Heidlas, J. E.; Lees, W. J.; Pale, P.; Whitesides, G. M. J. Org. Chem. 1992, 57, 146-151. (l) Simon, E. S.; Grabowski, S.; Whitesides, G. M. J. Org. Chem. 1990, 55, 1834-1841. (m) Toone, E. J.; Simon, E. S.; Whitesides, G. M. J. Org. Chem. 1991, 56, 5603-5606. (n) Shames, S. L.; Simon, E. S.; Christopher, C. W.; Schmid, W.; Whitesides, G M.; Yang. L.-L. Glycobtology 1991, 1, 187-191. (o) Shen, G.-J.; Liu, J. L.-C.; Wong, C.-H. Biocatalysis 1992, 6, 31-42.
24. Chemical synthesis: (a) Kochetkov, N. K.; Shibaev, V. N. In Advances in carbohydrate chemistry and biochemistry; Tipson, R. S., Horton, D., Eds.; Academic Press: New York, 1973; Vol. 28, pp 307-399. (b) Ichikawa, Y.; Sim, M. M.; Wong, C.-H. J. Org. Chem. 1992, 57, 2943-2946. (c) Sim, M. M., Kondo, H.; Wong, C. H. J. Am. Chem. Soc. 1993, 115, 2260-2267. (d) Schmidt, R. R; Wegmann, B.; Jung, K.-H. Liebigs Ann. Chem. 1991, 2, 121-124. (e) Gokhale, U. B.; Hindsgaul. O.; Palcic, M. M. Can. J. Chem. 1990, 68, 1063-1071. (f) Klaffke, W. Carbohydr. Res. 1995, 266, 285-292. (g) Arlt, M.; Hindsgaul, O. J. Org. Chem. 1995, 60, 14-15. Enzymatic synthesis: (h) Toone, E. J.; Whitesides, G. M. Am. Chem. Soc. Symp. Ser. 1991, 466, 1-22. (i) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry. In Tetrahedron Organic Chemistry Series, Vol. 12; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science: Oxford, U. K., 1994; pp252-311. (j) Heidlas, J. E.: Lees, W. J.; Whitesides, G M. J. Org. Chem. 1992, 57, 152-157. (k) Heidlas, J. E.; Lees, W. J.; Pale, P.; Whitesides, G. M. J. Org. Chem. 1992, 57, 146-151. (l) Simon, E. S.; Grabowski, S.; Whitesides, G. M. J. Org. Chem. 1990, 55, 1834-1841. (m) Toone, E. J.; Simon, E. S.; Whitesides, G. M. J. Org. Chem. 1991, 56, 5603-5606. (n) Shames, S. L.; Simon, E. S.; Christopher, C. W.; Schmid, W.; Whitesides, G M.; Yang. L.-L. Glycobtology 1991, 1, 187-191. (o) Shen, G.-J.; Liu, J. L.-C.; Wong, C.-H. Biocatalysis 1992, 6, 31-42.
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