title: Sequentially photocleavable protecting groups in solid-phase synthesis.
abstract: [reaction: see text] A sequential solid-phase peptide synthesis was developed using both photolabile linker and protecting groups. The chromatic sequential lability between a tert-butyl ketone-derived linker (sensitive to irradiation at 305 nm) and a nitroveratryloxycarbonyl (NVOC) group (sensitive at 360 nm) was exploited to prepare Leu-Enkephalin in a 55% overall yield. This new strategy allows the preparation of peptides in essentially neutral medium, by avoiding the use of common deprotection reagents such as trifluoroacetic acid or piperidine.
authors.affiliation: Department of Chemistry, University of Basel, 19 St. Johanns-Ring, CH-4056 Basel, Switzerland.
authors.forename: Martin
authors.initials: M
authors.lastname: Kessler
authors.forename: Ralf
authors.initials: R
authors.lastname: Glatthar
authors.forename: Bernd
authors.initials: B
authors.lastname: Giese
authors.forename: Christian G
authors.initials: CG
authors.lastname: Bochet