Abstract
Abstract Lariat ethers bearing N-pivot dipeptide arms have been designed and synthesized as models of natural amino acid and Na+ cation carriers, the “symporters”. Two types of dipeptide derived lariats have been prepared: those having amino terminal dipeptide arms (ATD-lariats, 6, 7, 10, 11, 16–18) and those having carboxylic group terminal dipeptide arms (CTD-lariats, 12, 19). ATD-lariats were synthesized by N-acylation of aza-15-crown-5, aza-18-crown-6, and 4,13-diaza-18-crown-6 with Z-GlyOH or Z-PhgOH (Phg = d-α-phenylglycine) in the presence of DCC or Ph3P/CCl4/Et3N condensation agents, subsequent hydrogenolytic removal of Z-protecting groups, and the introduction of a second Z-amino acid unit using the same condensation reagents. CTD-lariats 12 and 19 were obtained by N-alkylations of aza-18-crown-6 and 4,13-diaza-18-crown-6 with methyl N-(chloro-acetyl)-d-α-phenylglycinate (acetonitrile, Na2CO3, NaI). The binding affinities of ATD-lariats toward Na+ and K+ assessed in anh. MeOH and compared with th...
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