Synthesis of cyclic peptides from unprotected precursors using removable Nα-(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 molecul...

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Bibliographic Details
Published in:The journal of peptide research 2003-03, Vol.61 (3), p.152-157
Main Authors: Cardona, V.M.F., Hartley, O., Botti, P.
Format: Article
Language:English
Subjects:
chemical ligation
Chromatography, High Pressure Liquid
Dimethylformamide - chemistry
Esters - chemistry
Glycine - chemistry
Hydrogen-Ion Concentration
Methylene Chloride - chemistry
Models, Chemical
Peptide Biosynthesis
peptide cyclization
Peptides - chemistry
Protein Structure, Tertiary
Resins, Synthetic
solid-phase synthesis
Time Factors
Trifluoroacetic Acid - chemistry
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Summary:: 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.
ISSN:1397-002X
1399-3011
DOI:10.1034/j.1399-3011.2003.00043.x