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  • Title: [Direct tert-butylation of tryptophan: preparation of 2,5,7-tri-tert-butyltryptophan (author's transl)].
    Author: Löw M, Kisfaludy L, Jaeger E, Thamm P, Knof S, Wönsch E.
    Journal: Hoppe Seylers Z Physiol Chem; 1978 Dec; 359(12):1637-42. PubMed ID: 738697.
    Abstract:
    The tert-butylation of free tryptophan under simulated conditions of acidolytic cleavage of protecting groups being based on a tert-butyl moiety does finally yield the tri-substituted amino acid as a main product, namely 2,5,7-tri-tert-butyltryptophan. The structural elucidation of this substance and other tert-butylated products, which were isolated mostly in a pure form, was achieved by means of spectroscopic methods, in particular mass spectrometry and nuclear magnetic resonance spectroscopy.
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