1996 BADER-AWARD-LECTURE - AMINOACYL ETHYL PHOSPHATES - BIOMIMETICALLY ACTIVATED AMINO-ACIDS

Aminoacyl ethyl phosphates are functional analogues of aminoacyl adeny lates, the activated intermediates formed by ribosomal enzymes from th e reaction of amino acids with ATP. The aminoacyl ethyl phosphates are prepared by DCC-mediated coupling of a tetraalkyammonium salt of ethy l phosphate and an N-t-Boc-amino acid, followed by deprotection. The e fficiency of the synthesis and the solubility properties of the produc t depend on the alkyl group in the ammonium counterion of the phosphat e. N-Protected and free aminoacyl ethyl phosphates hydrolyze slowly (t (1/2), in neutral solution, 25 degrees C, similar to 100 h). These mat erials are potentially useful in biomimetic peptide synthesis, protein modification, and aminoacylation of RNA.