An important side reaction using the thiol, 3,6-dioxa-1,8-octanedithiol (DODT), in 9-fluorenylmethoxycarbonyl-based solid phase peptide synthesis

作者：Harris Paul W R^*; Kowalczyk Renata; Yang Sung Hyun; Williams Geoffrey M; Brimble Margaret A

来源：Journal of Peptide Science, 2014, 20(3): 186-190.

DOI：10.1002/psc.2595

• peptide cleavage
• 3
• 6-dioxa-1
• 8-ocatanedithiol
• methionine
• alkylation

A considerable quantity of an alkylation by-product is observed when using 3,6-dioxa-1,8-octanedithiol as a scavenger during acidic release of peptides containing the thioether amino acid methionine from the solid support. Adjustment of the cleavage conditions by replacement of 3,6-dioxa-1,8-octanedithiol with ethane dithiol or by using methionine sulfoxide as an alternative to methionine resulted in no such impurity. The by-product was detectable by liquid chromatography and mass spectrometry and characterised by NMR spectroscopy of an isolated model peptide. It could be effectively removed in a separate post cleavage step by treatment with dilute aqueous acid at 37 degrees C.

• 出版日期2014-3