(1-PYRENYL)METHYL CARBAMATES FOR FLUORESCENT "CAGED" AMINO ACIDS AND PEPTIDES

A highly fluorescent 1-pyrenylmethyloxycarbonyl amino acid (Pmoc-amino acid) is obtained in moderate yield by the reaction of (1-pyrenylmethyl)-4-nitrophenylcarbonate with an amino acid in the presence of sodium carbonate. The condensation of Pmoc-amino acid with an amino acid gives Pmoc-peptide in the presence of 1-ethyl-3-(3-dimethylaminepropyl)carbodiimide and 1-hydroxyben-zotriazole. The amino acid is recovered from an H₂O-dioxane (2:3) solution of Pmoc-amino acid by irradiation through a Pyrex filter with a medium pressure Hg lamp or at 340 nm. Although the quantum yield of the photolysis is rather low (ca 0.01), the photolysis proceeds fast and efficiently due to the large absorption coefficient of Pmoc-amino acid at around 340 nm. Thus, the use of Pmoc-amino acid as a “caged” amino acid is promising.