Staudinger Ligation of Peptides at Non-Glycyl Residues
نویسندگان
چکیده
منابع مشابه
Staudinger ligation of peptides at non-glycyl residues.
The Staudinger ligation provides a means to form an amide bond between a phosphinothioester and azide. This reaction holds promise for the ligation of peptides en route to the total chemical synthesis of proteins. (Diphenylphosphino)methanethiol is the most efficacious of known reagents for mediating the Staudinger ligation of peptides, providing high (> 90%) isolated yields for equimolar coupl...
متن کاملDNA conjugation by Staudinger ligation.
Two 5 modified 2'-deoxyuridin triphosphates and a 7 modified 2'-deoxy-7-deazaadenosine were synthesized carrying a terminal azide linked to the base. For probing the sterical influence on incorporation and Staudinger ligation different sized flexible linkers were chosen. All three nucleotides can completely replace their natural counterparts in primer extension as well as polymerase chain react...
متن کاملProtein 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...
متن کاملMicrowave-assisted chemical ligation of S-acyl peptides containing non-terminal cysteine residues.
An efficient approach for the synthesis of a series of S-acyl peptides containing internal cysteine residues has been developed and the chemical long-range ligation of these S-acyl peptides via 5-, 8-, 11- and 14-membered cyclic transition states has been investigated. Our results include the first examples of successful isopeptide ligations starting from S-acyl peptides containing non-terminal...
متن کاملStereoselective N-glycosylation by Staudinger ligation.
Stereoselective methods for the chemical synthesis of beta-N-glycosyl amides are needed to generate glycopeptides and glycoproteins. Here, we report that the Staudinger ligation can be used to form glycosylated asparagine derivatives. The reaction proceeds with high stereoselectivity, and a variety of glycosyl azides can function as substrates. Our results provide precedence for the use of this...
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ژورنال
عنوان ژورنال: The Journal of Organic Chemistry
سال: 2006
ISSN: 0022-3263,1520-6904
DOI: 10.1021/jo0620056