Synthesis of alanyl nucleobase amino acids and their incorporation into proteins

Talukder Poulami; Dedkova Larisa M.; Ellington Andrew D.Yakovchuk PetroLim JaebumAnslyn Eric V.Hecht Sidney M.

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Synthesis of alanyl nucleobase amino acids and their incorporation into proteins

机译：Synthesis of alanyl nucleobase amino acids and their incorporation into proteins

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Proteins which bind to nucleic acids and regulate their structure and functions are numerous and exceptionally important. Such proteins employ a variety of strategies for recognition of the relevant structural elements in their nucleic acid substrates, some of which have been shown to involve rather subtle interactions which might have been difficult to design from first principles. In the present study, we have explored the preparation of proteins containing unnatural amino acids having nucleobase side chains. In principle, the introduction of multiple nucleobase amino acids into the nucleic acid binding domain of a protein should enable these modified proteins to interact with their nucleic acid substrates using Watson-Crick and other base pairing interactions. We describe the synthesis of five alanyl nucleobase amino acids protected in a fashion which enabled their attachment to a suppressor tRNA, and their incorporation into each of two proteins with acceptable efficiencies. The nucleobases studied included cytosine, uracil, thymine, adenine and guanine, i.e. the major nucleobase constituents of DNA and RNA. Dihydrofolate reductase was chosen as one model protein to enable direct comparison of the facility of incorporation of the nucleobase amino acids with numerous other unnatural amino acids studied previously. The Klenow fragment of DNA polymerase I was chosen as a representative DNA binding protein whose mode of action has been studied in detail. (C) 2016 Elsevier Ltd. All rights reserved.

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《Bioorganic and medicinal chemistry》 |2016年第18期|4177-4187|共11页
作者
Talukder Poulami; Dedkova Larisa M.; Ellington Andrew D.Yakovchuk PetroLim JaebumAnslyn Eric V.Hecht Sidney M.;
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作者单位

Arizona State Univ, Biodesign Ctr BioEnerget, Tempe, AZ 85287 USA;

Univ Texas Austin, Dept Chem, Austin, TX 78712 USA;

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正文语种英语
中图分类药学;
关键词
Nucleobases; DNA protein interaction; N-Boc-L-serine beta-lactone; DNA polymerase I;

Synthesis of alanyl nucleobase amino acids and their incorporation into proteins

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