Abstract: In this paper, a series of new chiral macrocyclic phosphoramidates containing 2,5-diaryl- 1,3,4-oxadizole and (S)-methylbenzylamine and L-amino acid methyl ester units were synthesized and the structures were determined by 1H NMR, MS, IR spectra and elemental analyses. FABMS, NMR and IR techniques were used to study the molecular recognition phenomena. The phosphoramidate molecules can form hydrogen bond or aromatic π-π interaction with D-phenylglycine, L-phenylglycine or L-phenylalanine methyl ester hydrochloride and dipeptide according to the appearance of 1+1 host guest molecular peak in FABMS spectra, NMR chemical shift and coupling constant changes. The chiral molecular recognition ability of chiral macrocyclic phosphoramidate for D-phenylglycine methyl ester hydrochloride is stronger than L-phenylglycine methyl ester hydrochloride. The side chain also affect the recognition ability, smaller substituent is better than larger substituent for the recongnition. As for the guest molecules, the {D-phenylglycine} and L-phenylglycine methyl ester hydrochloride are better than D- or L-phenylalanine methyl ester hydrochloride for the recongnition, no inclusion for the D- or L-alanine and L-histine methyl ester hydrochloride.

Key words: Phosphoramidate, Molecular recognition, Macrocyclic compound