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Volumn 69, Issue 10, 2004, Pages 3578-3581

Pseudoamide-Type Pyrrolidine and Pyrrolizidine Glycomimetics and Their Inhibitory Activities against Glycosidases

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITION; ENZYMES; GLYCOLS; UREA;

EID: 3242796921     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0499221     Document Type: Article
Times cited : (51)

References (48)
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  • 8
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    • Although the term "azasugar" is widely used in the literature to refer to glycomimetics where the endocyclic oxygen atom has been replaced by nitrogen, the term is not strictly correct according to the IUPAC-IUMB nomenclature recommendations for carbohydrates, the accepted term being "iminosugar". "Azahexose" would actually imply that a carbon atom has been exchanged for a nitrogen atom. See: McNaught, A. D. Pure Appl. Chem. 1996, 68, 1919.
    • (1996) Pure Appl. Chem. , vol.68 , pp. 1919
    • McNaught, A.D.1
  • 9
    • 0037832251 scopus 로고    scopus 로고
    • For recent reviews on iminosugar glycosidase inhibitors, see: (a) Asano, N. Curr. Top. Med. Chem. 2003, 3, 471.
    • (2003) Curr. Top. Med. Chem. , vol.3 , pp. 471
    • Asano, N.1
  • 13
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    • Alkaloid Glycosidase Inhibitors
    • Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford
    • (e) Elbein, A. D.; Molyneux, R. J. Alkaloid Glycosidase Inhibitors. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Elsevier: Oxford, 1999; Vol. 3, p 129.
    • (1999) Comprehensive Natural Products Chemistry , vol.3 , pp. 129
    • Elbein, A.D.1    Molyneux, R.J.2
  • 14
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    • Taxonomic Distribution of Iminosugars in Plants and Their Biological Activities
    • Stütz, A., Ed.; Wiley-VCH: Weinheim, Germany
    • (f) Simmonds, M. S. J.; Kite, G. C.; Porter, E. A. Taxonomic Distribution of Iminosugars in Plants and Their Biological Activities. In Iminosugars as Glycosidase Inhibitors; Stütz, A., Ed.; Wiley-VCH: Weinheim, Germany, 1999; p 8.
    • (1999) Iminosugars as Glycosidase Inhibitors , pp. 8
    • Simmonds, M.S.J.1    Kite, G.C.2    Porter, E.A.3
  • 15
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    • (g) Ossor, A.; Elbein, A. D. Glycoprotein Processing Inhibitors. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinaÿ, P., Eds.; Wiley-VCH: Weinheim, Germany, 2000; Part II, Vol. 3, p 513.
    • (2000) Carbohydrates in Chemistry and Biology , vol.3 , Issue.PART II , pp. 513
    • Ossor, A.1    Elbein, A.D.2
  • 16
    • 0000986987 scopus 로고    scopus 로고
    • Toward Azaglycosyl Compounds and Homoazaglycosides
    • Chapleur, Y., Ed.; Wiley-VCH: Weinheim, Germany
    • (a) Martin, O. R. Toward Azaglycosyl Compounds and Homoazaglycosides. In Carbohydrate Mimics. Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, Germany, 1998; p 259.
    • (1998) Carbohydrate Mimics. Concepts and Methods , pp. 259
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  • 21
    • 0002022599 scopus 로고    scopus 로고
    • Azasugars: Chemistry and Their Biological Activity as Potential Anti-HIV Drugs
    • Witczak, Z. J., Nieforth, K. A., Eds.; Marcel Dekker: New York
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    • (1997) Carbohydrates in Drug Design , pp. 471
    • Van Den Broek, L.A.G.M.1
  • 22
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    • note
    • 2 character, typically a pseudoamide-type nitrogen.
  • 32
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    • 5-Azido-5-deoxy-D-fructopyranose derivatives have also been obtained from L-sorbose, an alternative starting material for DMDP synthesis; see: (a) Murphy, D. J. Chem. Soc. C 1967, 1732.
    • (1967) J. Chem. Soc. C , pp. 1732
    • Murphy, D.1
  • 42
    • 0003532642 scopus 로고    scopus 로고
    • Tables of Glycosidase Inhibitors with Nitrogen in the Sugar Ring and Their Inhibitory Activities
    • Stütz, A., Ed.; Wiley-VCH: Weinheim, Germany
    • Ekhart, C. W.; Fechter, M. H.; Hadwiger, P.; Mlaker, E.; Stütz, A. E.; Tauss, A., Wrodnigg, T. M. Tables of Glycosidase Inhibitors with Nitrogen in the Sugar Ring and Their Inhibitory Activities. In Iminosugars as Glycosidase Inhibitors; Stütz, A., Ed.; Wiley-VCH: Weinheim, Germany, 1999; p 253.
    • (1999) Iminosugars as Glycosidase Inhibitors , pp. 253
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  • 43
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    • Glycosidase Inhibition by Basic Sugar Analogues and the Transition State of Enzymatic Glycoside Hydrolysis
    • Stütz, A., Ed.; Wiley-VCH: Weinheim
    • Theoretical and experimental studies indicate that true transition state analogues must be essentially neutral or zwitterionic at physiological pH to keep specificity against the target enzyme. See: (a) Legler, G. Glycosidase Inhibition by Basic Sugar Analogues and the Transition State of Enzymatic Glycoside Hydrolysis. In Iminosugars as Glycosidase Inhibitors; Stütz, A., Ed.; Wiley-VCH: Weinheim, 1999; p 31
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    • Legler, G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.