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Synthesis and characterization of an unnatural boron and nitrogen-containing tryptophan analogue and its incorporation into proteins.

ABSTRACT: A boron and nitrogen containing unnatural analogue of tryptophan is synthesized through the functionalization of BN-indole. The spectroscopic properties of BN-tryptophan are reported with respect to the natural tryptophan, and the incorporation of BN-tryptophan into proteins expressed in E. coli using selective pressure incorporation is described. This work shows that a cellular system can recognize the unnatural, BN-containing tryptophan. More importantly, it presents the first example of an azaborine containing amino acid being incorporated into proteins.

SUBMITTER: Boknevitz K

PROVIDER: S-EPMC6524624 | biostudies-literature | 2019 May

REPOSITORIES: biostudies-literature

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Synthesis and characterization of an unnatural boron and nitrogen-containing tryptophan analogue and its incorporation into proteins.

Boknevitz Katherine K Italia James S JS Li Bo B Chatterjee Abhishek A Liu Shih-Yuan SY

Chemical science 20190415 19

A boron and nitrogen containing unnatural analogue of tryptophan is synthesized through the functionalization of BN-indole. The spectroscopic properties of BN-tryptophan are reported with respect to the natural tryptophan, and the incorporation of BN-tryptophan into proteins expressed in <i>E. coli</i> using selective pressure incorporation is described. This work shows that a cellular system can recognize the unnatural, BN-containing tryptophan. More importantly, it presents the first example o ...[more]

PMID: 31183048

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