[Direct tert-butylation of tryptophan: preparation of 2,5,7-tri-tert-butyltryptophan (author's transl)].
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.
D055598:Chemical Phenomena; D002621:Chemistry; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008722:Methods; D010455:Peptides / Q000138:chemical synthesis; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014364:Tryptophan / Q000031:analogs & derivatives*
C018683:2,5,7-tri-tert-butyltryptophan; D010455:Peptides; D014364:Tryptophan
Direkte tert-Butylierung des Tryptophans. Herstellung von 2,5,7-Tri-tert-butyltryptophan.