A chiral acetylene monomer having a cholesteryl group (PSCh) and novel three types of chiral acetylene monomers having a o-substituted tyrosine methyl ester (PSMY-Rs: -COC(6)H(5)=PSMY-Bz; -COC(6)H(4)CN=PSMY-BzCN; -COC(12)H(9)=PSMY-PhBz) as a pendant group were synthesized from 4-oxo-4-(prop-2-ynyloxy)butanoic acid (PS), and polymerized with the rhodium-catalyzed system. Structures and properties of the monomers and the resulting polymers were characterized and evaluated by NMR, IR, GPC, and DSC. In addition, these optical properties were investigated by polarimetric detector and circular dichroism (CD) analyses.