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Título: | 2-Methoxy-4-methylsulfinylbenzyl Alcohol as a Safety-Catch Linker for the Fmoc/tBu Solid-Phase Peptide Synthesis Strategy |
Autor: | Nandhini, K. P.; Albericio, Fernando CSIC ORCID; de la Torre, Beatriz G. | Palabras clave: | Solid-Phase Peptide Synthesis (SPPS) Trifluoroacetic acid (TFA) |
Fecha de publicación: | 5-ago-2022 | Editor: | American Chemical Society | Citación: | The Journal of Organic Chemistry 87 (15): 9433–9442 (2022) | Resumen: | Fmoc and Boc group are the two main groups used to protect the α-amino function in Solid-Phase Peptide Synthesis (SPPS). In this regard, the use of the Mmsb linker allows the combination of these two groups. Peptide-O-Mmsb-Resin is stable to the piperidine and trifluoroacetic acid (TFA) treatment used to remove Fmoc and Boc, respectively. The peptide is detached in a two-step protocol, namely reduction of the sulfoxide to the sulfide with Me3SiCl and Ph3P, and then treatment with TFA. The advantage of this strategy has been demonstrated by the following: preparation of peptide with no diketopiperazine formation in sequences prone to this side reaction; on-resin cyclization without the concourse of common organic reagents such as Pd(0) but of difficult use in a biological laboratory; and on-resin disulfide formation in a total side-chain unprotected peptide. The use of Mmsb linker together with Msib (4-(methylsulfinyl)benzyl) and Msbh (4,4'-bis(methylsulfinyl)benzhydryl) described in the accompanying manuscript add a fourth dimension to the SPPS protecting group scheme. | Versión del editor: | https://doi.org/10.1021/acs.joc.2c01057 | URI: | http://hdl.handle.net/10261/310408 | DOI: | 10.1021/acs.joc.2c01057 | ISSN: | 00223263 |
Aparece en las colecciones: | (IQAC) Artículos |
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acs.joc.2c01057.pdf | Artículo principal | 2,56 MB | Adobe PDF | Visualizar/Abrir |
jo2c01057_si_001.pdf | Material suplementario | 864,73 kB | Adobe PDF | Visualizar/Abrir |
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