Spirolactams as conformationally restricted pseudopeptides: synthesis and conformational analysis |
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Authors: | Fernández M Montserrat Diez Anna Rubiralta Mario Montenegro Elvira Casamitjana Núria Kogan Marcelo J Giralt Ernest |
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Institution: | Departament de Química Orgànica, Facultat de Química, Universitat de Barcelona, c/Martí i Franquès, Spain. |
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Abstract: | The synthesis of 1-(tert-butoxycarbonyl)-7-1-(tert-butoxycarbonyl)-3-methylbutyl]-6-oxo-1,7-diazaspiro4.5]decanes (S,S)-1a and (S,R)-1b is described. Derivatives 17a,b and 19a are prepared for use in peptide synthesis as constrained surrogates of the Pro-Leu and Gly-Leu dipeptides. The Ac-Gly-Leu]-Met-NH(2) derivatives (S,S,S)-2a and (S,R,S)-2b, with the tripeptidic C-terminal region present in tachykinins, are also synthesized. Conformational analyses of these tripetide analogues by NMR experiments and molecular modeling calculations show that both (S,S,S)-2a and (S,R,S)-2b epimers are gamma-turn/distorted type II beta-turn mimetics. |
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