DESIGN, SYNTHESIS AND EVALUATION OF A NOVEL BICYCLIC LACTAM AS A GLY-PRO TYPE-VI BETA-TURN MIMIC

被引:0
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作者
DUMAS, JP [1 ]
GERMANAS, JP [1 ]
机构
[1] UNIV HOUSTON,DEPT CHEM,HOUSTON,TX 77204
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中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselective synthesis and conformational evaluation of Gly-Pro type VI turn mimic 7, the first mimetic to constrain the central three bonds and incorporate the side chain groups of a beta-turn, is described. A superimposition of the crystallographically determined structure of 7 with the structure of a typical type VI turn revealed exceptional similarity in backbone and side chain atom positions. The temperature dependence of the chemical shift of the amide proton of the derivative 8 in DMSO confirmed the presence of a remarkably stable i, i+3 intramolecular hydrogen bond.
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页码:1493 / 1496
页数:4
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