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Practical, laboratory‐scale synthesis of N in ‐formyl tryptophan hydrobromide
Author(s) -
Chulin Alexey N.,
Rodionov Igor L.
Publication year - 2014
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.2613
Subject(s) - hydrobromide , tryptophan , chemistry , scale (ratio) , combinatorial chemistry , biochemistry , organic chemistry , geography , amino acid , cartography
A range of inorganic and organoelement halides was evaluated as acidic promoters of direct N in ‐formylation of tryptophan. In addition to Me 3 SiBr, the less expensive PBr 3 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. Copyright © 2014 European Peptide Society and John Wiley & Sons, Ltd.