Journal
INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS
Volume 16, Issue 3, Pages 133-144Publisher
SPRINGER
DOI: 10.1007/s10989-010-9215-y
Keywords
Anti-obesity; AOD9604; Cyclic peptides; Dicarba peptides; Ring closing metathesis (RCM); Microwave irradiation; Pseudoproline (Psi Pro) residues
Categories
Funding
- Australian Postgraduate Research Award
- AINSE
- CSIRO
- Australian Research Council
- Circardian Technologies Ltd.
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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 (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.
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