Synthesis of cyclic peptides from unprotected precursors using removable N alpha-(1-(4-methoxyphenyl)-2-mercaptoethyl) auxiliary.
A new method to cyclize unprotected peptides is presented. The method involves the use of a 1-phenyl-2-mercaptoethyl derivative on the N-terminal glycine. This template acts as an auxiliary thiol-containing group in order to drive cyclization with a counterpart thioester moiety on the same molecule. Subsequent facile removal of the derivative generates products with only native peptide structure. The successful, high-yield cyclization of the peptide GSPYSSDTTPA is described.
Cardona
V M F
VM
Department of Medical Biochemistry, University Medical Center, Geneva, Switzerland.
Hartley
O
O
Botti
P
P
D002851:Chromatography, High Pressure Liquid; D004126:Dimethylformamide / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005998:Glycine / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D008752:Methylene Chloride / Q000737:chemistry; D008956:Models, Chemical; D010452:Peptide Biosynthesis; D010455:Peptides / Q000737:chemistry*; D017434:Protein Structure, Tertiary; D012117:Resins, Synthetic; D013997:Time Factors; D014269:Trifluoroacetic Acid / Q000737:chemistry
D004952:Esters; D010455:Peptides; D012117:Resins, Synthetic; D008752:Methylene Chloride; D004126:Dimethylformamide; D014269:Trifluoroacetic Acid; D005998:Glycine