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Untersuchungen über den N in -Formylrest als mögliche Schutzgruppe gegen Tryptophan-tert-Butylierung

1979; De Gruyter; Volume: 360; Issue: 1 Linguagem: Inglês

10.1515/bchm2.1979.360.1.13

0018-4888

Miklós Löw, L. Kisfaludy,

Amino Acid Enzymes and Metabolism

Investigations on the Nin-formyl group as a protecting group of the tryptophan indole side chain under the conditions of conventional peptide synthesis using model compounds are described. The protecting group prevents the tert-butylation of tryptophan residues during acidolytic removal of tert-butyloxycarbonyl groups and allows the preparation of tryptophan tert-butylester in good yields. However, because of the observed side reactions, as hydrogenation of the indole to a 2,3-dihydroindole side chain, instability of the protecting group under various experimental conditions, the Nin-formyl group is only of limited use in peptide synthesis.