title: Efficient preparation of Fmoc-aminoacyl-N-ethylcysteine unit, a key device for the synthesis of peptide thioesters.
abstract: The synthesis of Fmoc-aminoacyl-N-ethyl-S-triphenylmethylcysteine, an N- to S-acyl migratory device for the preparation of peptide thioesters by Fmoc-SPPS (solid-phase peptide synthesis) is described. Condensation of Fmoc-aminoacyl pentafluorophenyl ester and N-ethyl-S-triphenylmethylcysteine was efficiently performed in the presence of HOOBt (3-hydroxy-3,4-dihydro-4-oxo-1,2,3-benzotriazine) in DMF. A small amount of diastereomer yielded during the reaction was easily separated by HPLC purification and the highly pure devices were obtained for most of the proteinogenic amino acids.
authors.affiliation: Department of Applied Biochemistry, Institute of Glycoscience, Tokai University, 4-1-1 Kitakaname, Hiratsuka, Kanagawa 259-1292, Japan. hojo@keyaki.cc.u-tokai.ac.jp
authors.forename: Hironobu
authors.initials: H
authors.lastname: Hojo
authors.forename: Hajime
authors.initials: H
authors.lastname: Kobayashi
authors.forename: Risa
authors.initials: R
authors.lastname: Ubagai
authors.forename: Yuya
authors.initials: Y
authors.lastname: Asahina
authors.forename: Yuko
authors.initials: Y
authors.lastname: Nakahara
authors.forename: Hidekazu
authors.initials: H
authors.lastname: Katayama
authors.forename: Yukishige
authors.initials: Y
authors.lastname: Ito
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Nakahara
mesh_terms: D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D003545:Cysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D010455:Peptides; D013438:Sulfhydryl Compounds; D003545:Cysteine