New TFA-Free Cleavage and Final Deprotection in Fmoc Solid-Phase Peptide Synthesis: Dilute HCl in Fluoro Alcohol

A novel method for cleaving from resin and removing acid-labile protecting groups for the Fmoc solid-phase peptide synthesis is described. 0.1 N HCl in hexafluoroisopropanol or trifluoroethanol cleanly and rapidly removes the tert-butyl ester and ether, Boc, trityl, and Pbf groups and cleaves the co...

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Bibliographic Details
Published in:Organic letters 2012-12, Vol.14 (24), p.6346-6349
Main Authors: Palladino, Pasquale, Stetsenko, Dmitry A
Format: Article
Language:English
Subjects:
Esters
Molecular Structure
Peptides - chemical synthesis
Peptides - chemistry
Resins, Synthetic - chemistry
Solid-Phase Synthesis Techniques
Trifluoroacetic Acid - chemistry
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Description
Summary:A novel method for cleaving from resin and removing acid-labile protecting groups for the Fmoc solid-phase peptide synthesis is described. 0.1 N HCl in hexafluoroisopropanol or trifluoroethanol cleanly and rapidly removes the tert-butyl ester and ether, Boc, trityl, and Pbf groups and cleaves the common resin linkers: Wang, HMPA, Rink amide, and PAL. Addition of just 5–10% of a hydrogen-bonding solvent considerably retards or even fully inhibits the reaction. However, a non-hydrogen-bonding solvent is tolerated.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol303124r