Diastereoselective synthesis and estimation of the conformational flexibility of 6-oxoperhydropyridazine-3-carboxylic acid derivatives |
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Authors: | Alvarez-Ibarra Carlos Csákÿ Aurelio G Gómez de la Oliva Cristina |
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Institution: | Departamento de Química Orgánica, Facultad de Química, Universidad Complutense, 28040-Madrid, Spain. |
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Abstract: | alpha,beta-Didehydroglutamates have been diastereoselectively transformed into 6-oxoperhydropyridazine-3-carboxylic acid derivatives (OPCAs), which constitute a new class of cyclic amino acid derivatives. Acylation at N-1 renders dipeptides which show considerable conformational rigidity. Semiempirical calculations suggest that OPCAs might force peptide turns with different amplitudes depending on the substitution pattern and relative stereochemistry of the substituents of the pyridazinone ring. |
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