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Volumn 62, Issue 21, 1997, Pages 7489-7494

New electronic analogs of the sialyl cation: N-functionalized 4-acetamido-2,4-dihydroxypiperidines. Inhibition of bacterial sialidases

Author keywords

[No Author keywords available]

Indexed keywords

ANIMAL KINGDOM; ANOMERIC CARBON; BINDING INTERACTION; CARBOXYL GROUPS; CELL SURFACES; GLYCOSIDASE INHIBITION; GLYCOSIDIC LINKAGES; N-ACETYLNEURAMINIC ACID;

EID: 0001679817     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo9708497     Document Type: Article
Times cited : (41)

References (61)
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    • Academic Press: New York
    • (d) Gotttschalk, A.; Bhargava, A. S. The Enzymes; Academic Press: New York, 1971; Vol. 5, pp 321-342.
    • (1971) The Enzymes , vol.5 , pp. 321-342
    • Gotttschalk, A.1    Bhargava, A.S.2
  • 35
    • 84892602085 scopus 로고    scopus 로고
    • Rat liver α(2→6)-sialyltransferase affords β-dideuterium kinetic isotope effects consistent with a transition state having oxocarbenium ion character. Unpublished results
    • Rat liver α(2→6)-sialyltransferase affords β-dideuterium kinetic isotope effects consistent with a transition state having oxocarbenium ion character. Horenstein, B. A., Bruner, M. Unpublished results.
    • Horenstein, B.A.1    Bruner, M.2
  • 36
    • 0030952095 scopus 로고    scopus 로고
    • We do not intend to imply that an aglycon or nucleophile is not part of the transition state for the reaction; it is a convenient artifice of inhibitor design to separate these peripheral transition state structural features from the core N-acetylneuraminyl unit which serves as a charge mimic. For a pertinent example of glycosyltransferase inhibitor design, see
    • (a) We do not intend to imply that an aglycon or nucleophile is not part of the transition state for the reaction; it is a convenient artifice of inhibitor design to separate these peripheral transition state structural features from the core N-acetylneuraminyl unit which serves as a charge mimic. (b) For a pertinent example of glycosyltransferase inhibitor design, see: Hashimoto, H.; Endo, T.; Kajihara, Y. J. Org. Chem. 1997, 62, 1914-1915.
    • (1997) J. Org. Chem. , vol.62 , pp. 1914-1915
    • Hashimoto, H.1    Endo, T.2    Kajihara, Y.3
  • 42
    • 84892583872 scopus 로고    scopus 로고
    • note
    • Direct attachment of a carboxylate residue to nitrogen is not appropriate as the resulting carbamic acid would not be stable. The methylene bridge between the carboxylate and secondary nitrogen increases the distance between the carboxylate and anomeric carbon mimic by ∼1.1 Å relative to the C-COO- bond length for N-acetylneuraminic acid.
  • 43
    • 0016468366 scopus 로고
    • A similar transformation of a 1,2-isopropylidene xylofuranoside to the ribofuranoside has been reported
    • A similar transformation of a 1,2-isopropylidene xylofuranoside to the ribofuranoside has been reported: Ritzmann, G.; Klein, R. S.; Hollenberg, D. H.; Fox, J. J. Carbohydr. Res. 1975, 39, 227-236.
    • (1975) Carbohydr. Res. , vol.39 , pp. 227-236
    • Ritzmann, G.1    Klein, R.S.2    Hollenberg, D.H.3    Fox, J.J.4
  • 48
    • 84892624477 scopus 로고    scopus 로고
    • Obtained by reduction of azide 12 to the amine with Raney nickel, N-acetylation, desilylation, and O-acetylation. X-ray: Manuscript in prepration
    • Obtained by reduction of azide 12 to the amine with Raney nickel, N-acetylation, desilylation, and O-acetylation. X-ray: Abboud, K.; Parr, I. B.; Horenstein, B. A. Manuscript in prepration.
    • Abboud, K.1    Parr, I.B.2    Horenstein, B.A.3
  • 53
    • 84949066052 scopus 로고
    • 1H NMR spectra which showed a multiplet at δ 7.5-8.0 consisting of four hydrogens. For an example of aromatization of a poly(hydroxypiperidine) , see: Rahman, A. U., Ed.; Elsevier: Amsterdam
    • 1H NMR spectra which showed a multiplet at δ 7.5-8.0 consisting of four hydrogens. For an example of aromatization of a poly(hydroxypiperidine) , see: Nishimura, Y. In Studies in Natural Products Chemistry; Rahman, A. U., Ed.; Elsevier: Amsterdam, 1992; pp 495-578.
    • (1992) Studies in Natural Products Chemistry , pp. 495-578
    • Nishimura, Y.1
  • 54
    • 84892615498 scopus 로고    scopus 로고
    • note
    • (a) Racemic compounds were synthesized since we did not wish to make initial assumptions regarding which stereoisomer might ultimately afford the better inhibitor. (b) Synthesis of side chain analogs raises the synthetic complexity by requiring discrimination between the two hydroxyl groups of compounds 5 or precursors.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.