Efficient reagent-saving method for the N-terminal labeling of bioactive peptides with organometallic carboxylic acids by solid-phase synthesis
| العنوان: | Efficient reagent-saving method for the N-terminal labeling of bioactive peptides with organometallic carboxylic acids by solid-phase synthesis |
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| المؤلفون: | Jack C. Slootweg, Daniel Siegmund, Nils Metzler-Nolte, H. Bauke Albada |
| المصدر: | Organometallics, 35(18), 3192-3196 Organometallics 35 (2016) 18 |
| سنة النشر: | 2016 |
| مصطلحات موضوعية: | chemistry.chemical_classification, 010405 organic chemistry, Biomolecule, Organic Chemistry, Chemical biology, Conjugated system, 010402 general chemistry, 01 natural sciences, Combinatorial chemistry, Organische Chemie, 0104 chemical sciences, Inorganic Chemistry, Acylation, chemistry.chemical_compound, Solid-phase synthesis, chemistry, Yield (chemistry), Reagent, Peptide synthesis, Life Science, Organic chemistry, Physical and Theoretical Chemistry |
| الوصف: | Labeling of biomolecules with organometallic moieties holds great promise as a tool for chemical biology and for the investigation of biochemical signaling pathways. Herein, we report a robust and reproducible synthetic strategy for the synthesis of ruthenocenecarboxylic acid, giving the acid in 53% overall yield. This organometallic label was conjugated via solid-phase peptide synthesis in near-quantitative yield to a number of different biologically active peptides, using only 1 equiv of the acid and coupling reagents, thereby avoiding wasting the precious organometallic acid. This optimized method of stoichiometric N-terminal acylation was then also successfully applied to conjugating ferrocenecarboxylic acid and a novel organometallic ReI(CO)3 complex, showing the generality of the synthetic procedure. |
| وصف الملف: | application/octet-stream; application/pdf |
| اللغة: | English |
| تدمد: | 0276-7333 |
| DOI: | 10.1021/acs.organomet.6b00544 |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_dedup___::bafc91b3816841a2bbeed9a393800270 https://doi.org/10.1021/acs.organomet.6b00544 |
| Rights: | RESTRICTED |
| رقم الانضمام: | edsair.doi.dedup.....bafc91b3816841a2bbeed9a393800270 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 02767333 |
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| DOI: | 10.1021/acs.organomet.6b00544 |