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Examples for the chemoenzymatic synthesis of analogues using purified glycosyltransferases: (a) Losey, H. C.; Peczuh, M. W.; Chen, Z.; Eggert, U. S.; Dong, S. D.; Pelczer, I.; Kahne, D.; Walsh, C. T. Biochemistry 2001, 40, 4745-4755. (b) Losey, H. C.; Jiang, J.; Biggins, J. B.; Oberthür, M.; Ye, X.-Y.; Dong, S. D.; Kahne, D.; Thorson, J. S.; Walsh, C. T. Chem. Biol. 2002, 9, 1305-1314. (c) Fu, X.; Albermann, C.; Jiang, J.; Liao, J.; Zhang, C.; Thorson, J. S. Nature Biotechnol. 2003, 21, 1467-1469. (d) Albermann, C.; Soriano, A.; Jiang, J.; Vollmer, H.; Biggins, J. B.; Barton, W. A.; Lesniak, J.; Nikolov, D. B.; Thorson, J. S. Org. Lett. 2003, 5, 933-936.
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Examples for the chemoenzymatic synthesis of analogues using purified glycosyltransferases: (a) Losey, H. C.; Peczuh, M. W.; Chen, Z.; Eggert, U. S.; Dong, S. D.; Pelczer, I.; Kahne, D.; Walsh, C. T. Biochemistry 2001, 40, 4745-4755. (b) Losey, H. C.; Jiang, J.; Biggins, J. B.; Oberthür, M.; Ye, X.-Y.; Dong, S. D.; Kahne, D.; Thorson, J. S.; Walsh, C. T. Chem. Biol. 2002, 9, 1305-1314. (c) Fu, X.; Albermann, C.; Jiang, J.; Liao, J.; Zhang, C.; Thorson, J. S. Nature Biotechnol. 2003, 21, 1467-1469. (d) Albermann, C.; Soriano, A.; Jiang, J.; Vollmer, H.; Biggins, J. B.; Barton, W. A.; Lesniak, J.; Nikolov, D. B.; Thorson, J. S. Org. Lett. 2003, 5, 933-936.
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11
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4444371956
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note
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NDP = nucleotide diphosphoryl; TDP = thymidine diphosphoryl; TMP = thymidine monophosphoryl; UDP = uridine diphosphoryl.
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12
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0034710989
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Recently, two TDP β-2-deoxy-L-sugars were synthesized enzymatically: (a) TDP epi-vancosamine: Chen, H.; Thomas, M. G.; Hubbard, B. K.; Losey, H. C.; Walsh, C. T.; Burkart, M. D. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 11942-11947. (b) TDP L-olivose: Amann, S.; Dräger, G.; Rupprath, C.; Kirschning, A.; Elling, L. Carbohydr. Res. 2001, 335, 23-32.
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Burkart, M.D.6
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13
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0034856716
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Recently, two TDP β-2-deoxy-L-sugars were synthesized enzymatically: (a) TDP epi-vancosamine: Chen, H.; Thomas, M. G.; Hubbard, B. K.; Losey, H. C.; Walsh, C. T.; Burkart, M. D. Proc. Natl. Acad. Sci. U.S.A. 2000, 97, 11942-11947. (b) TDP L-olivose: Amann, S.; Dräger, G.; Rupprath, C.; Kirschning, A.; Elling, L. Carbohydr. Res. 2001, 335, 23-32.
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0034693085
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This problem is also encountered in the construction of β-2-deoxy O-glycosides. For approaches to overcome this problem, see for example: Marzabadi, C. H.; Franck, R. W. Tetrahedron 2000, 56, 8385-8417.
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Franck, R.W.2
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19
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4444337813
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note
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Coupling is conducted at pH > 7; therefore, no acid-catalyzed product equilibration should occur.
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21
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84985297652
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Köpper, S.; Lundt, I.; Pedersen, C.; Thiem, J. Liebigs Ann. Chem. 1987, 531-535.
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24
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4444341474
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note
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2, tetrazole; (2) mCPBA) did not generate the dibenzyl phosphate.
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25
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4444233432
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note
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β). For complete NMR data, see Supporting Information.
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26
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4444302371
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note
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3 function was used in the coupling reaction, a decrease in β-selectivity was observed. Therefore, azido derivatives were used for all nitrogen-containing 2-deoxy sugars.
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28
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4444222040
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Lu, W.; Leimkuhler, C.; Oberthür, M.; Kahne, D.; Walsh, C. T. Biochemistry 2004, 43, 4548-4558.
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