Incorporation of Ahc into model dipeptides as an inducer of a β-turn with a distorted amide bond. Conformational analysis

…, JH Busto, JM Peregrina, F Rodríguez

文献索引：Avenoza, Alberto; Busto, Jesus H.; Peregrina, Jesus M.; Rodriguez, Fernando Journal of Organic Chemistry, 2002 , vol. 67, # 12 p. 4241 - 4249

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被引用次数: 29

摘要

The proline residue of dipeptides Ser-Pro and Pro-Ser has been replaced by 7-azabicyclo [2.2. 1] heptane-1-carboxylic acid (Ahc), a conformationally restricted analogue of proline that is capable of mimicking distorted amides. The conformational analysis of the new peptides in the solid state revealed that the Ahc-Ser sequence displays a type I β-turn, which includes a distorted amide bond. In contrast, the Ser-Ahc sequence exists in a nonfolded ...