Stereochemical effect of the amino acid side chain on the formation of penta-coordinate phosphorus intermediates from N-phosphorylamino acids:: A theoretical study

The stereochemical effect of the chiral amino acid residues on the formation of penta-coordinate phosphorus intermolecular mixed carboxylic-phosphoric anhydride (IMCPA) from N-phosphorylamino acids was studied with density functional theory (DFIP) calculations at B3LYP/6-311G(d,p) level. The reaction pathways for the formation of penta-coordinate phosphorus intermediates with different configurations through the carboxyl oxygen on amino acid group attacking the phosphoryl group from different directions were simulated and the stereoselectivity in the formation of IMCPA was discussed.