caa a22 4500 463186052 CHVBK 20180406164853.0 cr unu---uuuuu 170326e20070701xx s 000 0 eng 10.1007/s00726-006-0421-z doi (NATIONALLICENCE)springer-10.1007/s00726-006-0421-z Protease-catalyzed synthesis of the tripeptide CCK26-28, a fragment of CCK-8 [Elektronische Daten] [L. P. Meng, R. Joshi, H. Eckstein] Summary.: Two enzymatically synthetic strategies of the tripeptide derivative PhAc-Asp(OMe)-Tyr-Met-OAl are reported. The second strategy gains the advantage of more economical starting materials, less reaction steps and a higher overall isolated yield of this tripeptide fragment over the first strategy. The effect of the acyl-donor ester concentration and structure, the C-α protecting group of the nucleophile, reaction media, enzyme and the carrier on the tripeptide derivative synthesis were studied. This tripeptide selected is a fragment of the cholecystokinin C-terminal octapeptide (CCK-8), a potential therapeutic agent in the control of gastrointestinal function and also a drug candidate for the treatment of epilepsy. Springer-Verlag, 2006 Keywords: Enzymatic peptide synthesis - Immobilized enzymes - Organic solvent system - Solvent free system - CCK fragment nationallicence ACN : acetonitrile nationallicence AcONH4 : ammonium acetate nationallicence Al : allyl nationallicence Cam : carboxamidomethyl nationallicence CCK : cholecystokinin nationallicence CCK-8 : cholecystokinin C-terminal octapeptide nationallicence CHY : α-chymotrypsin nationallicence DCM : dichloromethane nationallicence DMF : dimethylformamide nationallicence Et : ethyl nationallicence EtOAc : ethyl acetate nationallicence FABMS : fast atom bombardment mass spectrometry nationallicence HPLC : high pressure liquid chromatography nationallicence Me : methyl nationallicence MPLC : middle pressure liquid chromatography nationallicence TEA : triethylamine nationallicence TFA : trifluoroacetic acid nationallicence Tos : p-tosylate nationallicence Tris : tris-(hydroxymethyl)-aminomethane nationallicence Rt : retention time in min nationallicence Z : benzyloxycarbonyl nationallicence Meng L. P. Pharmacy School of Tongji Medical College, HUST, Wuhan, China aut Joshi R. Institute of Organic Chemistry, University of Tübingen, Tübingen, Germany aut Eckstein H. Institute of Organic Chemistry, University of Tübingen, Tübingen, Germany aut Amino Acids Springer-Verlag 33/1(2007-07-01), 91-96 0939-4451 33:1<91 2007 33 726 https://doi.org/10.1007/s00726-006-0421-z text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s00726-006-0421-z text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Meng L. P. Pharmacy School of Tongji Medical College, HUST, Wuhan, China aut NATIONALLICENCE 700 1- Joshi R. Institute of Organic Chemistry, University of Tübingen, Tübingen, Germany aut NATIONALLICENCE 700 1- Eckstein H. Institute of Organic Chemistry, University of Tübingen, Tübingen, Germany aut NATIONALLICENCE 773 0- Amino Acids Springer-Verlag 33/1(2007-07-01), 91-96 0939-4451 33:1<91 2007 33 726 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer