Practical, laboratory-scale synthesis of N(in) -formyl tryptophan hydrobromide.
A range of inorganic and organoelement halides was evaluated as acidic promoters of direct N(in) -formylation of tryptophan. In addition to Me3 SiBr, the less expensive PBr3 was found to be highly efficient and was selected for further optimization. A convenient and reproducible synthetic procedure for N(in) -formyltryptophan hydrobromide developed in this way was scaled to 150 mmol and successfully extended to some derivatives of Trp and closely related indoles as detailed in the present paper. The scope of the method seems to be restricted to indoles substituted at C-3.
Laboratory of Peptide Chemistry, Branch of Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry RAS, 142290, Pushchino, 6 Science Avenue, Moscow region, Russia.
Alexey N
AN
Chulin
Igor L
IL
Rodionov
D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000138:chemical synthesis
C035643:N-formyltryptophan; D014364:Tryptophan
Trp(For); bromotrimethylsilane; indole ring, N-formylation; phosphorus tribromide