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

Zervosen, Astrid; Elling, Lothar

doi:10.1021/ja953495e

Article (Scientific journals)

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

Zervosen, Astrid; Elling, Lothar

1996 • In Journal of the American Chemical Society, 118 (8), p. 1836-1840

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10.1021/ja953495e

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Keywords :

LacNAc; in situ regeneration; enzymatic synthesis; beta-1,4-galactosyltransferase; alpha-2,6-sialyltransferase

Abstract :

[en] A new three-enzyme reaction cycle consisting of sucrose synthase, UDP glucose 4‘-epimerase, and human β-1,4-galactosyltransferase was established for the synthesis of N-acetyllactosamine (LacNAc) with in situ regeneration of UDP galactose. We found that UDP glucose 4‘-epimerase is reductively inactivated in the presence of UMP and acceptor substrates of β-1,4-galactosyltransferase. Reactivation of UDP glucose 4‘-epimerase by the transition state analogues dUDP or dTDP 6-deoxy-d-xylo-4-hexulose in combination with the repetitive batch technique enabled us to use the native enzymes for 11 days in this cycle. With 10 U of sucrose synthase, 5 U of UDP glucose 4‘-epimerase, and 1.25 U of β-1,4-galactosyltransferase, 594 mg of LacNAc could be synthesized. N-Acetyllactosamine was also subsequently converted to Neu5Acα2,6Galβl,4GlcNAc with α-2,6-sialyltransferase and CMP-Neu5Ac.

Disciplines :

Biochemistry, biophysics & molecular biology

Author, co-author :

Zervosen, Astrid ; Université de Liège - ULiège > Centre de recherches du cyclotron

Elling, Lothar

Language :

English

Title :

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

Publication date :

1996

Journal title :

Journal of the American Chemical Society

ISSN :

0002-7863

eISSN :

1520-5126

Publisher :

American Chemical Society, Washington, United States - District of Columbia

Volume :

118

Issue :

Pages :

1836-1840

Peer reviewed :

Peer Reviewed verified by ORBi

Available on ORBi :

since 23 July 2009

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Bibliography

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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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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