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Título: | Solid-Phase Synthesis of C-Terminus Cysteine Peptide Acids |
Autor: | Mthembu, Sinenhlanhla N.; Chakraborty, Amit; Schönleber, Ralph; Albericio, Fernando CSIC ORCID; De La Torre, Beatriz G. | Palabras clave: | Solid-phase peptide synthesis 4-methylpiperidine Epimerization Racemization Side reaction |
Fecha de publicación: | 15-nov-2022 | Editor: | American Chemical Society | Citación: | Organic Process Research and Development (2022) | Resumen: | Cysteine (Cys) is a key amino acid in many therapeutic peptides. For research and industrial purposes, solid-phase peptide synthesis is the method of choice for the preparation of most peptides. The solid-phase synthesis of C-terminal Cys peptide acids is problematic because it is accompanied by a side reaction, namely, the abstraction of α-H from the Cys residue, which leads to the formation of three side products: the epimer and two N-piperidinyl-Ala epimer peptides. Here, we used a chlorotrityl chloride resin to conduct a rational and in-depth study of this side reaction. The following variables were examined: removal of the fluorenylmethoxycarbonyl (Fmoc) group by different bases, the presence or absence of an acid rectifier for buffering the base, and thiol side-chain protection. In conclusion, the use of Fmoc-Cys protected with tetrahydropyran (Thp) and 4-methoxytrityl (Mmt) along with 30% 4-methylpiperidine in 0.5 M OxymaPure-DMF for Fmoc removal assures minimization of the side reaction, as demonstrated in a model peptide and confirmed for the elongation of somatostatin. | Versión del editor: | https://doi.org/10.1021/acs.oprd.2c00321 | URI: | http://hdl.handle.net/10261/284404 | DOI: | 10.1021/acs.oprd.2c00321 | ISSN: | 10836160 |
Aparece en las colecciones: | (IQAC) Artículos |
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acs.oprd.2c00321.pdf | Artículo principal | 2,99 MB | Adobe PDF | Visualizar/Abrir |
op2c00321_si_001.pdf | Material suplementario | 823,37 kB | Adobe PDF | Visualizar/Abrir |
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