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Volumn 6, Issue 6, 2004, Pages 897-900

S-linked ganglioside analogues for use in conjugate vaccines

Author keywords

[No Author keywords available]

Indexed keywords

CERAMIDE DERIVATIVE; GANGLIOSIDE; GANGLIOSIDE GM2; GANGLIOSIDE GM3; GLYCOSIDASE; LACTOSE; OLIGOSACCHARIDE; SIALIC ACID; THIOGLYCOSIDE; VACCINE;

EID: 1642528382     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036460p     Document Type: Article
Times cited : (74)

References (45)
  • 6
    • 0000406765 scopus 로고
    • Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, The Netherlands
    • (a) Defaye, J.; Gelas, J. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, The Netherlands, 1991; pp 315-357.
    • (1991) Studies in Natural Products Chemistry , pp. 315-357
    • Defaye, J.1    Gelas, J.2
  • 8
    • 84961328835 scopus 로고    scopus 로고
    • Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH: Toronto, Canada
    • (c) Fair-weather, J. K.; Driguez, H. In Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH: Toronto, Canada, 2000; Vol. 1, pp 531-564.
    • (2000) Carbohydrates in Chemistry and Biology , vol.1 , pp. 531-564
    • Fairweather, J.K.1    Driguez, H.2
  • 14
    • 1642479532 scopus 로고    scopus 로고
    • Doctoral Thesis, University of Alberta
    • Yu, H. N. Doctoral Thesis, University of Alberta, 2002.
    • (2002)
    • Yu, H.N.1
  • 15
    • 0038587638 scopus 로고    scopus 로고
    • Metabolically stable glycosides have recently been proposed for use in vaccines: (a) Kuberan, B.; Sikkander, S. A.; Tomiyama, H.; Linhardt, R. J. Angew. Chem., Int. Ed. 2003, 42, 2073-2075. (b) Bousquet, E.; Spadaro, A.; Pappalardo, M. S.; Bernardini, R.; Romeo, R.; Panza, L.; Ronsisvalle, G. J. Carbohydr. Chem. 2000, 19, 527-541.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 2073-2075
    • Kuberan, B.1    Sikkander, S.A.2    Tomiyama, H.3    Linhardt, R.J.4
  • 21
    • 1642561192 scopus 로고    scopus 로고
    • note
    • Alternatively, 8 could be obtained directly from the diol without purification of the sulfonate ester. Interestingly, some acetyl transfer to the 4′-OH (presumably originating from sulfur) was also observed in this case and 9 (7%) accompanied the formation of 8 (73%).
  • 38
    • 1642479525 scopus 로고    scopus 로고
    • note
    • Efforts to employ the anomeric thiolate of sialic acid as a nucleophile (see Scheme 1) to produce disaccharide 18 or trisaccharide 25 met with failure, only 2,3-elimination products were obtained.
  • 39
    • 1642438532 scopus 로고    scopus 로고
    • Doctoral Thesis. University of Alberta
    • Liu, L. Doctoral Thesis. University of Alberta, 2003.
    • (2003)
    • Liu, L.1
  • 44
    • 1642438531 scopus 로고    scopus 로고
    • note
    • This reaction has been observed for β-octyl, β-allyl, and β-8-methoxycarbonyloctyl galactosides and a variety of lactosides.
  • 45
    • 1642479524 scopus 로고    scopus 로고
    • note
    • 13C NMR data, including TROESY spectra.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.