C-Terminally modified peptides via cleavage of the HMBA linker by O-, N- or S-nucleophiles

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A large variety of C-terminally modified peptides was obtained by nucleophilic cleavage of the ester bond in solid phase linked peptide esters of 4-hydroxymethyl benzamide (HMBA). The developed methods provided peptides, C-terminally functionalized as esters, amides and thioesters, with high purity directly from the resin in a single reaction step. A comprehensive screening of the reaction conditions and scope for nucleophilic cleavage of peptides from the HMBA linker was performed.

Original languageEnglish
JournalOrganic & Biomolecular Chemistry
Issue number12
Pages (from-to)3238-3245
Number of pages8
Publication statusPublished - 2016

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