Tandem enzymatic resolution yielding L-alpha-aminoalkanedioic acid omega-esters.
The tandem action of serine protease (alpha-chymotrypsin or subtilisin BPN') and Aspergillus genus aminoacylase on racemic N-acetyl-alpha-aminoalkanedioic acid alpha,omega-diester produced L-alpha-aminoalkanedioic acid omega-ester in good yield and high optical purity. L-alpha-Aminosuberic acid omega-ester thus obtained was conveniently introduced into an oxytocin analog, [Asu1,6]oxytocin, by the solid-phase-synthesis and cyclization-cleavage method with oxime resin.
Nishino
N
N
Department of Applied Chemistry, Faculty of Engineering, Kyushu Institute of Technology, Kitakyushu, Japan.
Arai
T
T
Ueno
Y
Y
Ohba
M
M
D000581:Amidohydrolases / Q000378:metabolism; D000595:Amino Acid Sequence; D000600:Amino Acids, Dicarboxylic / Q000138:chemical synthesis* / Q000302:isolation & purification; D002851:Chromatography, High Pressure Liquid; D002918:Chymotrypsin / Q000378:metabolism; D004952:Esters / Q000138:chemical synthesis / Q000302:isolation & purification; D008969:Molecular Sequence Data; D010121:Oxytocin / Q000031:analogs & derivatives / Q000138:chemical synthesis; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D013381:Subtilisins / Q000378:metabolism
D000600:Amino Acids, Dicarboxylic; D004952:Esters; C010851:oxytocin, 1,6-alpha-Asu-; C019146:2-aminosuberic acid; D010121:Oxytocin; D013381:Subtilisins; D002918:Chymotrypsin; D000581:Amidohydrolases; C019672:aminoacylase I