Methods for enhancing ring closing metathesis yield in peptides: synthesis of a dicarba human growth hormone fragment

Bianca Van Lierop, Amanda Whelan, Sofianos Andrikopoulos, Roger Mulder, William Jackson, Andrea Robinson

Research output: Contribution to journalArticleResearchpeer-review

17 Citations (Scopus)

Abstract

Ruthenium-alkylidene catalysed ring closing metathesis (RCM) provides a convenient method for the synthesis of cyclic dicarba peptide analogues. Sequences devoid of turn-inducing residues, however, can often fail to cyclise. A combination of pseudoproline (IPro) insertion and microwave irradiation can be used to enhance RCM yield in these problematic sequences. This strategy is illustrated in the synthesis of a dicarba human growth hormone (hGH) fragment. The structural changes associated with cystine to dicarba replacement were found to change the metabolic profile of the peptide.
Original languageEnglish
Pages (from-to)133 - 144
Number of pages12
JournalInternational Journal of Peptide Research and Therapeutics
Volume16
Issue number3
DOIs
Publication statusPublished - 2010

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