Design, synthesis, and conformational analysis of azacycloalkane amino acids as conformationally constrained probes for mimicry of peptide secondary structures

Conformationally constrained amino acid and dipeptide units can serve in mi mics of specific secondary structures for studying relationships between pe ptide conformation and biological activity. A variety of mimics are require d to study systematically the structure-activity relationships in biologica lly relevant peptides. We present our efforts on the design, synthesis, and conformational analysis of a series of rigid surrogates of amino acid and dipeptide units for application within constrained peptide analogues, and f or employment as inputs for combinatorial science. Conceived to be general and versatile, our methodology has derived a variety of azacycloalkane and azabicycloalkane amino acids an enantiomerically pure form. via practical m ethods, from readily available and inexpensive starting materials. (C) 2000 John Wiley & Sons, Inc. Inc.