Sequentially photocleavable protecting groups in solid-phase synthesis
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Updated: Sep 26, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Martin Kessler1, Ralf Glatthar, Bernd Giese
1Department of Chemistry, University of Basel, 19 St. Johanns-Ring, CH-4056 Basel, Switzerland.
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.
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