title: Peptide synthesis by chymotrypsin in frozen solutions. Free amino acids as nucleophiles.
abstract: Nucleophilic efficiency of the free amino acids in chymotrypsin-catalyzed acyl transfer in ice at -18 degrees C using ethyl esters of N-maleyl-L-tyrosine and L-tyrosine as the acyl group donors has been studied. Although the amino acids did not act as acyl acceptors in liquid water, the high yields of peptides were obtained in frozen solutions at pH 10.5 (before freezing). The efficiency of amino acids in the formation of the corresponding dipeptides depended on the substrate used, and decreased in the order Ser,Thr,Gln > Lys > Cit > Ala > Ala > Gly > Asn > Arg > Glu > Val > Orn > Asp with no peptide formed with His, Leu, Ile and Pro) for N-maleyl-L-tyrosine ethyl ester and Ser > Lys > Orn > Arg,Cit > Gln > Thr > Asn > Ala > Gly (with no peptide formed with Glu, Val, Asp, His, Leu, Ile and Pro) for L-tyrosine ethyl ester.
authors.affiliation: Laboratory of Bioorganic Chemistry, Akadeemia 23, Tallinn, Estonia.
authors.forename: V
authors.initials: V
authors.lastname: Tõugu
authors.forename: H
authors.initials: H
authors.lastname: Meos
authors.forename: M
authors.initials: M
authors.lastname: Haga
authors.forename: A
authors.initials: A
authors.lastname: Aaviksaar
authors.forename: H D
authors.initials: HD
authors.lastname: Jakubke
mesh_terms: D000596:Amino Acids / Q000737:chemistry / Q000378:metabolism*; D002918:Chymotrypsin / Q000378:metabolism*; D004151:Dipeptides / Q000138:chemical synthesis*; D004563:Electrochemistry; D005615:Freezing; D006863:Hydrogen-Ion Concentration
chemical_list: D000596:Amino Acids; D004151:Dipeptides; D002918:Chymotrypsin