Chemical Ligation 2017
DOI: 10.1002/9781119044116.ch10
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Thioamide Labeling of Proteins through a Combination of Semisynthetic Methods

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Cited by 3 publications
(7 citation statements)
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“…Destabilizing effects in α-helices however, were comparatively mild, and some of the destabilizing effects in α-helices can be 'rescued' with the incorporation of a second thioamide. 140 However, the observed effects cannot fully be rationalized using crystal structures of the native proteins. Determining high-resolution structures of the thioamide proteins themselves will benefit the field substantially.…”
Section: Thioamide Effects In Full Length Proteinsmentioning
confidence: 99%
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“…Destabilizing effects in α-helices however, were comparatively mild, and some of the destabilizing effects in α-helices can be 'rescued' with the incorporation of a second thioamide. 140 However, the observed effects cannot fully be rationalized using crystal structures of the native proteins. Determining high-resolution structures of the thioamide proteins themselves will benefit the field substantially.…”
Section: Thioamide Effects In Full Length Proteinsmentioning
confidence: 99%
“…Although there have been various approaches to this problem, 135,141 the use of a 2% (v/ v) solution of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) seems to give the best combination of high deprotection efficiency and minimal epimerization. This is particularly important for the synthesis of peptides containing multiple adjacent thioamides, 137,142 motifs found in the thioviridamide family of compounds. While alternate methods such as recently developed ynamide-based couplings may lead to further improvements, 143 with these considerations, the thioacylbenzotriazoles can be used to access many thioamidecontaining peptides.…”
Section: ■ Thioamide Propertiesmentioning
confidence: 99%
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“…Alkyl dithioesters, thiobenzimidazolones, and thioacylnitrobenzotriazoles have been employed as active thioacylating reagents for thioamide-substituted peptide synthesis. Thioacylnitrobenzotriazoles prepared via a three-step transformations from natural α-amino acids (Figure , eq 1) make up the only class of thioacylating reagents that could be used to introduce a thioamide bond via solid phase peptide synthesis (SPPS). , However, this method is limited to 15 of the 20 common proteinogenic α-amino acids . In addition, the preparation of thioacylnitrobenzotriazole involves the use of toxic and malodour thionating reagents.…”
Section: Introductionmentioning
confidence: 99%