Lipase-catalyzed synthesis of O-lauroyl l-serinamide and O-lauroyl l-threoninamide

Abstract

O-Lauroyl l-serinamide and O-lauroyl l-threoninamide were synthesized with an immobilized lipase using lauric acid and l-serinamide or l-threoninamide in water-miscible organic solvents, of which 2-methyl-2-propanol gave the highest conversion of 93% for O-lauroyl l-serinamide at 50 mmol- l-serinamide/L and 100 mmol-lauric acid/L. The addition of 4 Å 1/16 molecular sieves at 50 mg/mL increased the conversion to 53% for O-lauroyl l-threoninamide at 50 mmol- l-threoninamide/L and 150 mmol-lauric acid/L in 2-methyl-2-butanol. The difference of conversion between the two products was exactly proportional to the difference of solubility of aminoacid amides.