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Volumn 10, Issue 12, 2008, Pages 2373-2376

Chemical synthesis of cyclic galactooligofuranosides isolated from enzymatic degradation products of cell wall arabinogalactan of Mycobacterium tuberculosis

Author keywords

[No Author keywords available]

Indexed keywords

ARABINOGALACTAN; BACTERIAL POLYSACCHARIDE; GALACTAN;

EID: 48849117687     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800530u     Document Type: Article
Times cited : (15)

References (27)
  • 1
    • 0037844364 scopus 로고    scopus 로고
    • For selected reviews on the structure of mycobacterial cell wall, see: a
    • For selected reviews on the structure of mycobacterial cell wall, see: (a) Brennan, P. J. Tuberculosis 2003, 83, 91-97.
    • (2003) Tuberculosis , vol.83 , pp. 91-97
    • Brennan, P.J.1
  • 5
    • 20144368306 scopus 로고    scopus 로고
    • For multi-drug resistance of M. tuberculosis strains, see: (a) Nettleman, M. D. JAMA 2005, 293, 2788-2790.
    • For multi-drug resistance of M. tuberculosis strains, see: (a) Nettleman, M. D. JAMA 2005, 293, 2788-2790.
  • 6
    • 0034702883 scopus 로고    scopus 로고
    • (b) Long, R. CMAJ 2000, 163, 425-428.
    • (2000) CMAJ , vol.163 , pp. 425-428
    • Long, R.1
  • 25
    • 59949091621 scopus 로고    scopus 로고
    • 2O to 15 would give a glycosyl triflate mixed anhydride, and then upon addition of Deoxofluor, the triflate would be displaced by the fluoride anion of Deoxofluor to provide a glycosyl carboxy fluoride intermediate. Finally, HF/pyridine would facilitate the lactonization of the carboxy fluoride to generate a glycosyl oxocarbenium ion, which would readily react with fluoride ion to afford glycosyl fluoride 18. In fact, we were able to isolate the glycosyl carboxy fluoride intermediate.
    • 2O to 15 would give a glycosyl triflate mixed anhydride, and then upon addition of Deoxofluor, the triflate would be displaced by the fluoride anion of Deoxofluor to provide a glycosyl carboxy fluoride intermediate. Finally, HF/pyridine would facilitate the lactonization of the carboxy fluoride to generate a glycosyl oxocarbenium ion, which would readily react with fluoride ion to afford glycosyl fluoride 18. In fact, we were able to isolate the glycosyl carboxy fluoride intermediate.
  • 26
    • 59949087286 scopus 로고    scopus 로고
    • 4 as the promoter for glycosyl fluoride, see: Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 431.
    • 4 as the promoter for glycosyl fluoride, see: Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 431.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.