期刊
INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS
卷 15, 期 4, 页码 247-253出版社
SPRINGER
DOI: 10.1007/s10989-009-9185-0
关键词
Formaldehyde; HF; Hydroxylamine; 2-Mercaptopyridine (2-PySH); Trifluoromethanesulfonic acid (TfOH)
During global deprotection using a strong acid in Boc chemistry, the electrophilic alkylating species, i.e. carbocations, and formaldehyde generated from the side-chain protecting groups and the benzyloxymethyl group on the His residue, respectively, can cause alkylation of susceptible residues. To reduce these side reactions, a deprotection procedure using a strong acid such as HF or trifuloromethanesulfonic acid must always be carried out in the presence of scavengers. We found that addition of hydroxylamine derivatives could efficiently suppress the side reactions associated with formaldehyde and that addition of 2-mercaptopyridine could not only specifically circumvent alkylation of the Met residue but also convert its sulfonium salt to the Met residue regardless of the substituent species.
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