Reduction of methionine sulfoxide in peptide synthesis by use of 2‐mercaptopyridine in liquid hydrogen fluoride
- 1 July 1982
- journal article
- research article
- Published by Wiley in International Journal of Peptide and Protein Research
- Vol. 20 (1) , 63-65
- https://doi.org/10.1111/j.1399-3011.1982.tb02653.x
Abstract
Methionine d-sulfoxide can be reduced to methionine in liquid HF in the presence of 2-mercaptopyridine. The utility of the reaction in peptide synthesis was demonstrated by preparation of the model peptide H-Leu-Gly-Arg-Leu-Gly-Met-Phe-OH (I) by the solid-phase method. When the peptide resin H-Leu-Gly-Arg(Tos)-Leu-Gly-Met(de-sulfoxide)-Phe-resin is treated in liquid HF in the presence of the standard scavenger anisole, H-Leu-Gly-Arg-Leu-Gly-Met(d-sulfoxide)-Phe-OH (II) is obtained in .apprx. 66% overall yield with no detectable trace of I. When the same peptide resin is treated in like manner in the added presence of 2-mercaptopyridine, I is obtained in .apprx. 63% overall yield with no detectable trace of II.Keywords
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