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Solid-phase synthesis of arginine-containing peptides and fluorogenic substrates using a side-chain anchoring approach.
J Org Chem
November 2004
Laboratoire des Aminoacides Peptides et Protéines, CNRS UMR 5810, Universités Montpellier I et II, Faculté de Pharmacie, 15 avenue Charles Flahault, BP 14491, 34093 Montpellier cédex 5, France.
Attachment of an amino acid to a solid support by its side chain is sometimes necessary to take advantage of an alpha-carboxylic group available for diverse modifications, including the incorporation of a fluorophore for the preparation of fluorogenic substrates. In contrast to most other amino acids, anchoring the guanidinium group of an arginine to a resin requires the use of a supplementary linker. To avoid the usually multistep synthesis of such a linker as well as its difficult attachment to the guanidine group, we developed a simple method where the guanidine group is built on a Rink amide resin.
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