Ornithine- and lysine-based novel N-propargylamides, N-alpha-tert-butoxycarbonyl-N-delta-fluorenylmethoxycarbonyl-L-ornithine -N'-propargylamide (1), N-alpha-tert-butoxycarbonyl-N-epsilon-fluorenylmethoxycarbonyl-L-lysine-N'-propargylamide (2), N-alpha-fluorenylmethoxycarbonyl-N-delta-tert-butoxycarbonyl-L-ornithine -N'-propargylamide (3), and N-alpha-fluorenylinethoxycarbonyl-N-epsilon-tert-butoxycarbonyl-L-lysine -N'-propargylamide (4) were synthesized and polymerized with a rhodium catalyst. Polymers with moderate molecular weights were obtained in good yields. Poly(1)-poly(4) showed strong Cotton effects in THF, whose sign and wavelength depended on the substituents. They were satisfactorily converted into the corresponding polymers [poly(1a) -poly (4a)] with free amino groups. Poly(1a) and poly(2a) also formed a helix, while poly(3a) and poly(4a) did not. Poly(1a) and poly(2a) decreased the CD intensity by the addition of m- and o-phthalic acids. (C) 2007 Elsevier Ltd. All rights reserved.