Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation

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Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation.

The introduction of chemically unique groups into proteins by means of non-natural amino acids has numerous applications in protein engineering and functional studies. One method to achieve this involves the utilization of a non-natural amino acid by the cell's native translational apparatus. Here we demonstrate that a methionine surrogate, azidohomoalanine, is activated by the methionyl-tRNA s...

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DNA 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...

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Phosphine-based redox catalysis in the direct traceless Staudinger ligation of carboxylic acids and azides.

The synthesis of amide C N bonds through nucleophilic acyl substitutions constitutes one of the most fundamental transformations in chemical synthesis. Recently, the Staudingertype ligation of carboxylic acid derivatives (e.g., acid chlorides, anhydrides, acyl selenides, and thioesters) and azides has become a preeminent strategy for amide C N bond construction (Scheme 1a). However, the generat...

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ژورنال

عنوان ژورنال: Proceedings of the National Academy of Sciences

سال: 2001

ISSN: 0027-8424,1091-6490

DOI: 10.1073/pnas.012583299