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Volumn 67, Issue 25, 2002, Pages 8862-8870

Synthesis and antituberculosis activity of C-phosphonate analogues of decaprenolphosphoarabinose, a key intermediate in the biosynthesis of mycobacterial arabinogalactan and lipoarabinomannan

Author keywords

[No Author keywords available]

Indexed keywords

ANTITUBERCULOSIS ACTIVITY;

EID: 0037073950     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026247r     Document Type: Article
Times cited : (62)

References (46)
  • 1
    • 0002722563 scopus 로고    scopus 로고
    • Mycobacterial cell wall components
    • Fraser-Reid, B., Tatsuta, K., Thiem, J., Eds.; Springer-Verlag: Berlin, Germany
    • (a) Lowary, T. L. Mycobacterial cell wall components. In Glycoscience: Chemistry and Chemical Biology; Fraser-Reid, B., Tatsuta, K., Thiem, J., Eds.; Springer-Verlag: Berlin, Germany, 2001; pp 2005-2080.
    • (2001) Glycoscience: Chemistry and Chemical Biology , pp. 2005-2080
    • Lowary, T.L.1
  • 19
    • 0031444647 scopus 로고    scopus 로고
    • Incorporation of arabinose into AG has been shown through the use of radiolabeled 3 and mycobacterial membrane extracts. In addition, incubation of small oligosaccharide substrates with 3, in the presence ofa mycobacterial membrane preparation, led to the formation of an oligesaccharide with additional β-(1→2) and α(1→5) linkages (Lee, R. E.; Brennan, P. J.; Besra, G. S. Glycobiology 1997, 7, 1121). The lack of α-(1→3) linkages was attributed to either instability or absence of α-(1→3) AraT activity in the membrane preparation, or the possibility that this enzyme recognizes oligosaccharide substrates larger than those investigated. It is also conceivable that another activated donor (e.g., a sugar nucleotide) is used by this AraT. The presence of UDP-Araf in mycobacteria has been reported (Singh, S.; Hogan S. E. Microbios 1994, 77, 217), but incorporation of this donor into arabinan has not been demonstrated.
    • (1997) Glycobiology , vol.7 , pp. 1121
    • Lee, R.E.1    Brennan, P.J.2    Besra, G.S.3
  • 20
    • 0028187872 scopus 로고
    • Incorporation of arabinose into AG has been shown through the use of radiolabeled 3 and mycobacterial membrane extracts. In addition, incubation of small oligosaccharide substrates with 3, in the presence ofa mycobacterial membrane preparation, led to the formation of an oligesaccharide with additional β-(1→2) and α(1→5) linkages (Lee, R. E.; Brennan, P. J.; Besra, G. S. Glycobiology 1997, 7, 1121). The lack of α-(1→3) linkages was attributed to either instability or absence of α-(1→3) AraT activity in the membrane preparation, or the possibility that this enzyme recognizes oligosaccharide substrates larger than those investigated. It is also conceivable that another activated donor (e.g., a sugar nucleotide) is used by this AraT. The presence of UDP-Araf in mycobacteria has been reported (Singh, S.; Hogan S. E. Microbios 1994, 77, 217), but incorporation of this donor into arabinan has not been demonstrated.
    • (1994) Microbios , vol.77 , pp. 217
    • Singh, S.1    Hogan, S.E.2
  • 22
    • 0002492589 scopus 로고    scopus 로고
    • Synthesis of glycosyl phosphate mimics
    • Chapleur, Y., Ed.; Wiley-VCH: Weinheim, Germany
    • Nicotra, F. Synthesis of glycosyl phosphate mimics. In Carbohydrate Mimics; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, Germany, 1998.
    • (1998) Carbohydrate Mimics
    • Nicotra, F.1
  • 43
    • 2242450768 scopus 로고    scopus 로고
    • note
    • 2, Pd/C, but were unsuccessful. Under these conditions, decomposition of the substrate was observed, which we attribute to the formation of a palladium-πallyl complex from the allyl phosphonate.
  • 44
    • 2242437366 scopus 로고    scopus 로고
    • note
    • Iatrobeads refers to a beaded silica gel 6RS-8060, which is manufactured by Iatron Laboratories (Tokyo).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.