title: Racemization-free synthesis of C-terminal cysteine-peptide using 2-chlorotrityl resin.
abstract: We investigated the effects of bases, resins, and S-protecting groups on the extent of racemization at the C-terminal cysteine during Fmoc-based(Fmoc=fluoren-9-yl-methoxy-carbonyl) solid phase peptide synthesis. The use of 2-chlorotrityl resin was most effective in suppressing the racemization caused by the base treatment for Fmoc-cleavage. Somatostatin was successfully synthesized with practically no racemization using 2-chlorotrityl resin by Fmoc-chemistry.
authors.affiliation: Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Japan.
authors.forename: Y
authors.initials: Y
authors.lastname: Fujiwara
authors.forename: K
authors.initials: K
authors.lastname: Akaji
authors.forename: Y
authors.initials: Y
authors.lastname: Kiso
mesh_terms: D002851:Chromatography, High Pressure Liquid; D003545:Cysteine / Q000737:chemistry*; D005449:Fluorenes; D007202:Indicators and Reagents; D007475:Ion Exchange Resins; D010455:Peptides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014320:Triphenylmethyl Compounds
chemical_list: D005449:Fluorenes; D007202:Indicators and Reagents; D007475:Ion Exchange Resins; D010455:Peptides; D014320:Triphenylmethyl Compounds; C071065:2-chlorotrityl chloride; C054007:1-(9-fluorenyl)methyl chloroformate; D003545:Cysteine