二肽
化学
部分
立体化学
二面角
戒指(化学)
肽
分子
氢键
生物化学
有机化学
作者
Timothy P. Burkholder,Edward W. Huber,Gary A. Flynn
标识
DOI:10.1016/s0960-894x(01)80882-9
摘要
6-Amino-5-oxo-7-pheynl-1,4-oxazepines were synthesized from β-phenylserine by a versatile route to provide gauche (−) phenylalanyl-X dipeptide mimetics (1a-h). NMR was utilized to elucidate the solution conformation of the protected mimetics. The seven membered ring was found to be in a chair conformation with the phtalimide moiety and the phenyl ring pseudo-equatorial, consistent with the gauche (−) conformation (dihedral angle X1 = −60°). Dipeptide mimetic 2 was synthesized from 1 a to probe the effect of the gauche (−) conformation on the inhibition of metalloproteinases. These gauche (−) dipeptide mimetics may be useful tools for the investigation of conformational preferences of enzyme substrates and receptor ligands.
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