DBU-catalyzed transprotection of N-Fmoc-cysteine di- and tripeptides into S-Fm-cysteine di- and tripeptides.
The transprotection of N-Fmoc-cysteine containing di- and tripeptides possessing a free SH group to produce the corresponding S-Fm-cysteine di- and tripeptides bearing a free amino group is accomplished efficiently with DBU in dry THF. The N-Fmoc to S-Fm transformation mechanism is discussed. S-Fm-Cysteine di- and tripeptides readily form amide bonds on coupling with N-(Pg-α-aminoacyl)benzotriazoles and N-(Pg-α-dipeptidoyl)benzotriazoles to give larger peptides.
Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA. katritzky@chem.ufl.edu
Alan R
AR
Katritzky
Nader E
NE
Abo-Dya
Abdelmotaal
A
Abdelmajeid
Srinivasa R
SR
Tala
M S
MS
Amine
Said A
SA
El-Feky
D002384:Catalysis; D003545:Cysteine / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry*; D015394:Molecular Structure; D009842:Oligopeptides / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D014508:Urea / Q000031:analogs & derivatives* / Q000737:chemistry
D004151:Dipeptides; D009842:Oligopeptides; D010455:Peptides; D014508:Urea; C483182:N,N'-dibutylurea; D003545:Cysteine