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Volumn 15, Issue 12, 2009, Pages 2747-2750

Efforts towards the identification of simpler platensimycin analogues-the total synthesis of oxazinidinyl platensimycin

Author keywords

Antibiotics enzymes; Medicinal chemistry; Platensimycin; Ring closing metathesis; Total synthesis

Indexed keywords

ANTIBIOTICS; CATALYSTS; ESTERS;

EID: 62349119695     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802568     Document Type: Article
Times cited : (46)

References (36)
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    • for total syntheses and synthetic studies towards platensimycin, see: b
    • for total syntheses and synthetic studies towards platensimycin, see: b) K.C. Nicolaou, A. Li, D.J. Edmonds, Angew. Chem. 2006, 118, 7244-7248;
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    • Nicolaou, K.C.1    Li, A.2    Edmonds, D.J.3
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    • For the biological activity of recently synthesized platensimycin analogues, see: a
    • For the biological activity of recently synthesized platensimycin analogues, see: a) K. C. Nicolaou, T. Lister, R. M. Denton, A. Montero, D.J. Edmonds, Angew. Chem. 2007, 119, 4796-4798;
    • (2007) Angew. Chem , vol.119 , pp. 4796-4798
    • Nicolaou, K.C.1    Lister, T.2    Denton, R.M.3    Montero, A.4    Edmonds, D.J.5
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    • The carbamate moiety of the oxazinidinyl ring can maintain the hydrogen-bonding interactions with A309 of ecFabF. The oxazinidinyl ring is however not strictly an isosteric replacement of the enone ring core of platensimycin due to the lack of the C4 methyl group found in the parent compound
    • The carbamate moiety of the oxazinidinyl ring can maintain the hydrogen-bonding interactions with A309 of ecFabF. The oxazinidinyl ring is however not strictly an isosteric replacement of the enone ring core of platensimycin due to the lack of the C4 methyl group found in the parent compound.
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    • The reductive amination was conducted in the polar protic solvent. MeOH; therefore dipole minimization might not play as great a role in product distribution
    • The reductive amination was conducted in the polar protic solvent. MeOH; therefore dipole minimization might not play as great a role in product distribution.
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    • Using the conventional and usual twofold dilution method, the MIC of oxazinidinyl platensimycin 2 for all the strains would be 128μg mL 1 because the determined MIC value of 90 μg mL 1 lies between 64 and 128 μg mL 1
    • 1.
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    • Platensimycin methyl ester is also not a potent antibiotic, see
    • Platensimycin methyl ester is also not a potent antibiotic, see: S. B. Singh, K. B. Herath, J. Wang, N. Tsou, R. G. Ball, Tetrahedron Lett. 2007, 48, 5429-5433.
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    • Singh, S.B.1    Herath, K.B.2    Wang, J.3    Tsou, N.4    Ball, R.G.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.