On the antibiotic activity of oxazolomycin

被引:25
作者
Bagwell, Claire L. [1 ]
Moloney, Mark G. [1 ]
Thompson, Amber L. [1 ]
机构
[1] Univ Oxford, Dept Chem, Chem Res Lab, Oxford OX1 3TA, England
关键词
oxazolomycin; antibiotic; bioactivity; conformation;
D O I
10.1016/j.bmcl.2008.05.105
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Structural analysis of oxazolomycin and simpler fragments containing a common 3-hydroxy-2,2-dimethylpropanamide moiety has indicated that a U-shaped conformation is preferred, in some cases stabilised by hydrogen bonding between the N-H and O-H residues, as shown by a combination of molecular modelling, NMR spectroscopic and single crystal X-ray analysis. A direct synthesis of this unit has been established via the opening of b-lactones by a range of amines, and their antibacterial activity been shown to vary with the hydrophobic character of the substituents. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4081 / 4086
页数:6
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