Insitu thioester formation for protein ligation using α-methylcysteine
نویسندگان
چکیده
منابع مشابه
N-methylcysteine-mediated total chemical synthesis of ubiquitin thioester.
Ubiquitin thioester is a key intermediate in the ubiquitylation of proteins and is formed enzymatically through the activation of alpha-COOH of ubiquitin in an ATP dependent manner using the E1 enzyme. The current methods used for the preparation of ubiquitin thioester rely on either the enzymatic machinery or on expressed protein ligation technology. In this article, we report a new chemical s...
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[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 ...
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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...
متن کاملSerine promoted synthesis of peptide thioester-precursor on solid support for native chemical ligation.
Fmoc solid phase peptide synthesis of thioesters for the chemical synthesis of proteins via native chemical ligation is a challenge. We have developed a versatile approach for direct synthesis of peptide thioesters from a solid support utilizing Fmoc chemistry. Peptide thioester synthesis is performed by the formation of a cyclic urethane moiety via a selective reaction of the backbone amide ch...
متن کاملProtein thioester synthesis enabled by sortase.
Proteins containing a C-terminal thioester are important intermediates in semisynthesis. Currently there is one main method for the synthesis of protein thioesters that relies upon the use of engineered inteins. Here we report a simple strategy, utilizing sortase A, for routine preparation of recombinant proteins containing a C-terminal (α)thioester. We used our method to prepare two different ...
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ژورنال
عنوان ژورنال: Chem. Sci.
سال: 2014
ISSN: 2041-6520,2041-6539
DOI: 10.1039/c3sc52140k