Switch peptide via Staudinger reaction.
نویسندگان
چکیده
A new transformation based on the Staudinger reaction is described, and its application in the design of a novel switch element to control peptide folding is demonstrated. We found that the azide switch is activated rapidly in water to promote acyl transfer using tris(2-carboxyethyl)phosphine hydrochloride (TCEP) via the Staudinger reaction. Our findings expand the repertoire of uses of the Staudinger reaction in chemical biology and the number of available triggers for use in switch peptides.
منابع مشابه
Nucleophilic metal complexes as acylation catalysts: solvent-dependent "switch" mechanisms leading to the first catalyzed Staudinger reaction.
[formula: see text] Catalytic acylation using complex transition metal salts MCo(CO)4 is demonstrated. Surprisingly, a solvent-dependent mechanistic "switch" results in a Lewis acid-based acylation mechanism in nonpolar media and a nucleophilic mechanism in polar organic media. These observations lead to the first example of a catalyzed Staudinger reaction to form beta-lactams.
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عنوان ژورنال:
- Organic letters
دوره 10 22 شماره
صفحات -
تاریخ انتشار 2008