β-Turn and β-hairpin mimicry with tetrasubstituted alkenes

RR Gardner, GB Liang, SH Gellman

Index: Gardner, Robb R.; Liang, Gui-Bai; Gellman, Samuel H. Journal of the American Chemical Society, 1999 , vol. 121, # 9 p. 1806 - 1816

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Citation Number: 84

Abstract

Synthesis and conformational analysis are reported for molecules containing the trans-5- amino-3, 4-dimethylpent-3-enoic acid residue (ADPA, 1). This amino acid is a glycylglycine mimic, in which the central amide group is replaced with an E-tetrasubstituted alkene. It was anticipated that this isosteric replacement would promote specific local (β-turn) and nonlocal (β-hairpin) conformational preferences. Previous work has shown that the most common β ...