Boron and nitrogen (BN) containing heterocycles, such as 1,2-azaborines, have an isosteric and isoelectronic relationship with their carbonaceous counterparts, marking them as ideal targets for biological and medicinal studies. Tryptophan, an essential amino acid, has been studied due to its importance in protein structure and stability, its role as the main source of intrinsic protein fluorescence, and its low abundance in proteins. Incorporation of a BN bond into tryptophan through a late stage functionalization of the BN-indole allows us to add a new analogue of tryptophan to the library of unnatural amino acids that have been used in the study of proteins. This poster will discuss the synthesis of BN-tryptophan, its properties in comparison with natural tryptophan, and its application as an unnatural amino acid.

Synthesis, characterization, and application of an unnatural boron and nitrogen containing isostere of tryptophan

255th National Meeting (2018)

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