Staudinger ligation: a peptide from a thioester and azide.
نویسندگان
چکیده
[reaction: see text] The technique of native chemical ligation enables the total chemical synthesis of proteins. This method is limited, however, by an absolute requirement for a cysteine residue at the ligation juncture. Here, this restriction is overcome with a new chemical ligation method in which a phosphinobenzenethiol is used to link a thioester and azide. The product is an amide with no residual atoms.
منابع مشابه
Protein Assembly Using the Staudinger Ligation
Introduction New methods are facilitating the total chemical synthesis of proteins. In particular, the chemical ligation of synthetic peptides provides a convergent route to proteins. Currently, the most common ligation method is “native chemical ligation” [1]. In native chemical ligation, the thiolate of an N-terminal cysteine residue of one peptide attacks the C-terminal thioester of a second...
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The traceless Staudinger ligation is an effective means to synthesize an amide bond between two groups of otherwise orthogonal reactivity: a phosphinothioester and an azide. An important application of the Staudinger ligation is in the ligation of peptides at a variety of residues. Here, we demonstrate that the traceless Staudinger ligation can be achieved in water with a water-soluble reagent....
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[figure: see text] The Staudinger ligation can be used to couple a peptide with a C-terminal phosphinothioester to another with an N-terminal alpha-azido group to form a single peptide that contains no residual atoms. Here diphenylphosphinomethanethiol thioesters are shown to give high isolated yields for this transformation. This finding provides precedent for a powerful and versatile new meth...
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Chemical synthesis harbors the potential to provide ready access to natural proteins as well as to create nonnatural ones. The Staudinger ligation of a peptide containing a C-terminal phosphinothioester with a peptide containing an N-terminal azide gives an amide with no residual atoms. This method for amide bond formation is orthogonal and complementary to other ligation methods. Herein, we de...
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ورودعنوان ژورنال:
- Organic letters
دوره 2 13 شماره
صفحات -
تاریخ انتشار 2000