Methods for Enhancing Ring Closing Metathesis Yield in Peptides: Synthesis of a Dicarba Human Growth Hormone Fragment
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- van Lierop, B.J., Whelan, A.N., Andrikopoulos, S. et al. Int J Pept Res Ther (2010) 16: 133. doi:10.1007/s10989-010-9215-y
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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 (ΨPro) 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.