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a,b-Dehydroamino Acids a , b -D e h y d r o a m i n o A c i d sAbstract: Dehydroamino acids are versatile intermediates in organic synthesis and occur as frequent structural motives in natural products and biologically active compounds. This review summarizes recent work (since 1999) on the synthesis, reactions and applications of acyclic and cyclic a,b-dehydroamino acids, a,bdehydroamino esters, and protected a,b-dehydroamino acids. 6Conclusions

[structure: see text] Methoxypyrrole amino acids (MOPAS) have been prepared and were introduced into small peptides with hairpin structures. The intra- and intermolecular binding properties of this heterocyclic amino acid mimicking a dipeptido beta-strand was investigated by NMR titration and X-ray crystal structure analysis. The data reveal a hydrogen bonding pattern that is complementary to a peptide beta-sheet.

A histidine-coordinating metal complex substituted with methoxypyrrole amino acids (MOPAS) as a peptide beta-sheet binder shows high affinity for a H(2)N-His-Leu-Leu-Val-Phe-OMe pentapeptide in DMSO solution. Within the complex, a beta-sheet conformation is induced into the pentapeptide by weak intra-assembly interactions with the MOPAS units.

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