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On choosing the right ether for peptide precipitation after acid cleavage
Author(s) -
de La Torre Beatriz G.,
Andreu David
Publication year - 2008
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.956
Subject(s) - peptide , cleavage (geology) , chemistry , ether , alkylation , peptide nucleic acid , methyl tert butyl ether , diethyl ether , ether cleavage , organic chemistry , nucleic acid , amino acid , peptide synthesis , combinatorial chemistry , biochemistry , catalysis , biology , paleontology , fracture (geology)
Methyl tert ‐butyl ether (MTBE) and diethyl ether (DEE) tend to be regarded as interchangeable for the ‘cold ether’ workup concluding the final acidolytic cleavage and deprotection step of solid‐phase peptide syntheses. However, the use of MTBE to precipitate peptides from strong acid solutions is shown to give rise to t ‐butyl alkylation byproducts, readily detectable by MALDI‐TOF MS. The problem can attain undesirable dimensions in the cleavage of peptide resins containing high proportions of aromatic residues, particularly in peptide nucleic acid (PNA) syntheses. In those cases, DEE workup is advisable, as it consistently leads to cleaner products. Copyright © 2007 European Peptide Society and John Wiley & Sons, Ltd.