Preparations, solution conformation and molecular structures of N,N'-ethylene-bridged dipeptides and their derivatives.
The solution conformations of novel dipeptides, methyl (2S, 3'S)-3-methyl-2-(2'-oxo-3'-isopropyl-1'-piperazinyl)-butanoate (EVV-OCH3), methyl (2S, 3'S)-3-phenyl-2-(2'-oxo-3'-benzyl-1'-piperazinyl) propionate (EFF-OCH3), and their derivatives (Boc-Gly-EVV-OH, Boc-Gly-EVV-Gly-OH, and Boc-Gly-EFF-OH), were studied by 1H NMR measurements and molecular mechanics calculations (1). The molecular structures of Boc-Gly-EVV-OH, Boc-Gly-EFF-OH, and the hydrochloride of EVV-OCH3 were determined by X-ray analyses. The conformations of the piperazinone rings and the side chains of these oligopeptides were clarified.
Department of Chemistry, Faculty of Science, Osaka City University, Japan.
Y
Y
Kojima
Y
Y
Ikeda
E
E
Kumata
J
J
Maruo
A
A
Okamoto
K
K
Hirotsu
K
K
Shibata
A
A
Ohsuka
D055598:Chemical Phenomena; D002627:Chemistry, Physical; D004151:Dipeptides / Q000737:chemistry*; D005030:Ethylenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000737:chemistry*; D011487:Protein Conformation; D012996:Solutions; D014961:X-Ray Diffraction
D004151:Dipeptides; D005030:Ethylenes; D010456:Peptides, Cyclic; D012996:Solutions; C071063:methyl 3-methyl-2-(2'-oxo-3'-isopropyl-1'-piperazinyl)butanoate; C071064:methyl 3-phenyl-3-(2'-oxo-3'-benzyl-1'-piperazinyl)propionate