Just Add Water:  A New Fluorous Capping Reagent for Facile Purification of Peptides Synthesized on the Solid Phase

Vittorio Montanari and Krishna Kumar*
Department of Chemistry, Tufts University, Medford, Massachusetts 02155
J. Am. Chem. Soc., 2004, 126 (31), pp 9528–9529
DOI: 10.1021/ja0479033
Publication Date (Web): July 14, 2004
Copyright © 2004 American Chemical Society

Abstract

Abstract Image

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.

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History

  • Published In Issue August 11, 2004
  • Received April 12, 2004

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