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Regeneration of aged DMF for use in solid‐phase peptide synthesis
Author(s) -
Magtaan Jordan Kevin,
Devocelle Marc,
Kelleher Fintan
Publication year - 2019
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.3139
Subject(s) - dimethylamine , chemistry , formic acid , dimethylformamide , solvent , trifluoroacetic acid , peptide synthesis , inert gas , inert , degradation (telecommunications) , impurity , combinatorial chemistry , amino acid , organic chemistry , biochemistry , telecommunications , computer science
Dimethylformamide (DMF), which is still the most commonly used solvent for Fmoc‐SPPS, has the potential for degradation over time on exposure to air (and water vapour) and storage, to give dimethylamine and formic acid impurities. In particular, dimethylamine can lead to unwanted deprotection of the fluorenylmethyloxycarbonyl (Fmoc) group during, for example, the initial loading of Fmoc amino acids in SPPS, which leads reduced calculated loading values. We have found that treatment of such aged DMF by simple sparging with an inert gas (N 2 ), or vacuum sonication, can regenerate the DMF in order to restore loading levels back to those found for newer, fresh, DMF samples.