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...

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Bibliographic Details
Published in:Journal of peptide science 2014-04, Vol.20 (4), p.266-269
Main Authors: Chulin, Alexey N, Rodionov, Igor L
Format: Article
Language:English
Subjects:
Magnetic Resonance Spectroscopy
Mass Spectrometry
Tryptophan - analogs & derivatives
Tryptophan - chemical synthesis
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Summary: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.
ISSN:1075-2617
1099-1387
DOI:10.1002/psc.2613