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Volumn 6, Issue 17, 2004, Pages 2873-2876

A practical method for the stereoselective generation of β-2-deoxy glycosyl phosphates

Author keywords

[No Author keywords available]

Indexed keywords

BETA 2 DEOXY GLYCOSYLPHOSPHATE DERIVATIVE; CHLORIDE; GLYCOSYLTRANSFERASE; NUCLEOTIDE; PHOSPHATE; UNCLASSIFIED DRUG;

EID: 4444349884     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049187f     Document Type: Article
Times cited : (37)

References (29)
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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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    • 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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    • note
    • NDP = nucleotide diphosphoryl; TDP = thymidine diphosphoryl; TMP = thymidine monophosphoryl; UDP = uridine diphosphoryl.
  • 12
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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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    • 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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    • 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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    • Marzabadi, C.H.1    Franck, R.W.2
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    • note
    • Coupling is conducted at pH > 7; therefore, no acid-catalyzed product equilibration should occur.
  • 24
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    • note
    • 2, tetrazole; (2) mCPBA) did not generate the dibenzyl phosphate.
  • 25
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    • note
    • β). For complete NMR data, see Supporting Information.
  • 26
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    • note
    • 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.