Synthesis of pyrimidine derivatives of amino acids using pig liver esterase and pancreas lipase.
The parent methyl ester of the N-1 substituted 5-chloropyrimidinone is hydrolysed by pig liver esterase to the corresponding carboxylic acid. The acid chloride was made with PCl5 in toluene, and coupling with benzyl and methyl esters of selected L-amino acids to the corresponding amides was done in dichloromethane in the presence of triethylamine. The benzyl and methyl ester protecting groups were hydrolysed with pancreas lipase or esterase in a pH-stat to yield the corresponding carboxylic acids.
Hagelin
G
G
Department of Chemistry, Nycomed AS, Oslo, Norway.
Laland
S G
SG
Undheim
K
K
D000596:Amino Acids / Q000138:chemical synthesis*; D000818:Animals; D043182:Carboxylesterase; D002265:Carboxylic Ester Hydrolases / Q000378:metabolism*; D008049:Lipase / Q000378:metabolism*; D008099:Liver / Q000201:enzymology*; D009682:Magnetic Resonance Spectroscopy; D010179:Pancreas / Q000201:enzymology*; D011743:Pyrimidines / Q000737:chemistry*; D013552:Swine
D000596:Amino Acids; D011743:Pyrimidines; D002265:Carboxylic Ester Hydrolases; D043182:Carboxylesterase; D008049:Lipase