Abstract
AbstractPhototryptophan is a new photoactivatable amino acid designed to be incorporated into tryptophan‐containing peptides for photoaffinity labeling. The synthesis of phototryptophan starts from 6‐bromoindole with the installation of an 1‐azi‐2,2,2‐trifluoroethyl moiety, followed by microwave‐assisted condensation with serine under mild conditions. Separation of the N‐acetylated enantiomers was possible by employing Aspergillus aminoacylase. Differential scanning calorimetry showed that phototryptophan is thermally stable up to 100 °C. Boc‐L‐Phototryptophan was used to assemble a diazirine analog of the marine natural product hemiasterlin.
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