Just add water: a new fluorous capping reagent for facile purification of peptides synthesized on the solid phase

Vittorio Montanari; Krishna Kumar

doi:10.1021/ja0479033

Just add water: a new fluorous capping reagent for facile purification of peptides synthesized on the solid phase

J Am Chem Soc. 2004 Aug 11;126(31):9528-9. doi: 10.1021/ja0479033.

Authors

Vittorio Montanari¹, Krishna Kumar

Affiliation

¹ Department of Chemistry, Tufts University, Medford, Massachusetts 02155, USA.

PMID: 15291542
DOI: 10.1021/ja0479033

Abstract

A novel fluorous capping reagent is introduced to facilitate purification during solid-phase peptide synthesis (SPPS). Reagent 1 is a trivalent iodonium salt that reacts vigorously with free amines to deliver a long-chain fluoroalkyl group. It has been used to tag all unreacted amines following the peptide coupling step in SPPS. The resulting fluoroalkylated amine is no longer able to couple in further peptide coupling steps and is also stable to standard peptide synthesis conditions. Deletion products are removed using flash fluorous chromatography to yield the pure, full-length peptide.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Chromatography, High Pressure Liquid
Hydrocarbons, Fluorinated / chemistry*
Onium Compounds / chemistry*
Peptides / chemical synthesis
Peptides / isolation & purification*

Substances

Hydrocarbons, Fluorinated
Onium Compounds
Peptides

Grants and funding

GM65500/GM/NIGMS NIH HHS/United States