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Volumn 14, Issue 17, 2004, Pages 4389-4393

Synthesis of an unusual branched-chain sugar, 5-C-methyl-L-idopyranose for SAR studies of pyranmycins: Implication for the future design of aminoglycoside antibiotics

Author keywords

Aminoglycoside antibiotics; Antibacterial; Branched chain sugar; Drug development; Pyranmycins

Indexed keywords

5 C METHYL LEVO IDOPYRANOSE; AMINOGLYCOSIDE ANTIBIOTIC AGENT; PYRAN DERIVATIVE; SUGAR; UNCLASSIFIED DRUG;

EID: 3843122215     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.06.064     Document Type: Article
Times cited : (18)

References (32)
  • 22
    • 3843062831 scopus 로고    scopus 로고
    • note
    • Hydrolysis of the acetyl groups of 5, followed by regioselective tosylation at O-6 and azide substitution afforded presumably an undesired 2,6-anhydro-l-idopyranose. Attempts to use phenylthio 2,3,4-tri-O-benzyl-l- idopyranoside were hampered by the low stereoselectivity of glycosylation
  • 23
    • 3843067035 scopus 로고    scopus 로고
    • note
    • 3 for azide substitution. Hydrolysis of the acetyl groups of 18e, followed by regioselective tosylation at O-6″ and azide substitution afforded presumably an undesired 2″,6″-anhydro-L-idopyranose as the ring III component
  • 24
    • 3843147645 scopus 로고    scopus 로고
    • note
    • Methods for dilution antimicrobial susceptibility testing for bacteria that grow aerobically. Approved standard M7-A5, and performance standards for antimicrobial disk susceptibility tests. Approved standard M2-A7, National Committee for Clinical Laboratory Standards, Wayne, PA
  • 25
    • 3843096472 scopus 로고    scopus 로고
    • note
    • The score function was based on Amber 96 force-field as implemented in HyperChem 7.0, and the solvent-accessible surface methodology to account for the hydration effects. The program was developed for drug design, not specifically for the calculation of absolute binding affinity. Therefore, we look for the tendency in binding rather than the meaning interpreted from the absolute numbers of binding: the lower the number, the better the binding
  • 26
    • 3843074619 scopus 로고    scopus 로고
    • note
    • The MIC values were about 2-folds higher than the reported values against S. aureus, for all the tested compounds including neomycin B, presumably due to the variation in the inoculated bacteria concentration. However, these values were consistent in duplicated tests and were normalized to the reported values based on the MIC of neomycin B for clearer comparison
  • 32
    • 3843084397 scopus 로고    scopus 로고
    • note
    • +]) m/e 499.2615; measure m/e 499.2605


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.