Sequentially photocleavable protecting groups in solid-phase synthesis.
[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.
Kessler
Martin
M
Department of Chemistry, University of Basel, 19 St. Johanns-Ring, CH-4056 Basel, Switzerland.
Glatthar
Ralf
R
Giese
Bernd
B
Bochet
Christian G
CG