Synthesis of D-Alanine Oligopeptides Catalyzed by D-Aminopeptidase in Non-Aqueous Media

Synthesis of D-alanine oligopeptides from D-alanine methylester hydrochloride has been demonstrated by use of immobilized D-aminopeptidase from Ochrobactrum anthropi (Achromobacter sp.) in non-aqueous media. D-Alanine dimer and trimer were obtained in 56% and 6% yield, respectively, when 250 mM of the substrate was incubated for 3 hours with urethane-prepolymer immobilized D-aminopeptidase (1.5 U/ml) and 3 equivalents of triethylamine in water-saturated toluene. The kcat of this reaction was calculated to be 19,500 (min−1), which is several ten thousand times greater than that of the known enzymatic syntheses of amino acid oligomers.

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