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Kessler M, Glatthar R, Giese B, et al. Sequentially photocleavable protecting groups in solid-phase synthesis. Org Lett. 2003;5(8):1179-81doi: 10.1021/ol027454g.
Kessler, M., Glatthar, R., Giese, B., & Bochet, C. G. (2003). Sequentially photocleavable protecting groups in solid-phase synthesis. Organic letters, 5(8), 1179-81. https://doi.org/10.1021/ol027454g
Kessler, Martin, et al. "Sequentially photocleavable protecting groups in solid-phase synthesis." Organic letters vol. 5,8 (2003): 1179-81. doi: https://doi.org/10.1021/ol027454g
Kessler M, Glatthar R, Giese B, Bochet CG. Sequentially photocleavable protecting groups in solid-phase synthesis. Org Lett. 2003 Apr 17;5(8):1179-81. doi: 10.1021/ol027454g. PMID: 12688713.
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Org Lett. 2003 Apr 17;5(8):1179-81. doi: 10.1021/ol027454g.

Sequentially photocleavable protecting groups in solid-phase synthesis.

Organic letters

Martin Kessler, Ralf Glatthar, Bernd Giese, Christian G Bochet

Affiliations

  1. Department of Chemistry, University of Basel, 19 St. Johanns-Ring, CH-4056 Basel, Switzerland.

PMID: 12688713 DOI: 10.1021/ol027454g

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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