Lipase-catalyzed synthesis of O-lauroyl L-serinamide and O-lauroyl L-threoninamide.

摘要

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 A 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.