3 years ago

Total Synthesis of the Highly N-Methylated Acetylene-Containing Anticancer Peptide Jahanyne

Total Synthesis of the Highly N-Methylated
Acetylene-Containing Anticancer Peptide Jahanyne
Margaret A. Brimble, Paul W. R. Harris, George Opiyo, Iman Kavianinia, Daniel P. Furkert, Freda F. Li, Andrew Siow
The first total synthesis of the highly N-methylated acetylene-containing lipopeptide jahanyne, an apoptosis-inducing natural product from marine cyanobacteria, is reported. A late-stage solution-phase coupling enabled introduction of the C-terminal ketone pyrrolidine moiety. A modified Fmoc solid-phase synthesis strategy was adopted to effectively couple multiple sterically hindered N-methylated amino acids while suppressing epimerization. The total synthesis has enabled confirmation of the proposed absolute configuration of natural jahanyne.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03925

DOI: 10.1021/acs.orglett.7b03925

You might also like
Discover & Discuss Important Research

Keeping up-to-date with research can feel impossible, with papers being published faster than you'll ever be able to read them. That's where Researcher comes in: we're simplifying discovery and making important discussions happen. With over 19,000 sources, including peer-reviewed journals, preprints, blogs, universities, podcasts and Live events across 10 research areas, you'll never miss what's important to you. It's like social media, but better. Oh, and we should mention - it's free.

  • Download from Google Play
  • Download from App Store
  • Download from AppInChina

Researcher displays publicly available abstracts and doesn’t host any full article content. If the content is open access, we will direct clicks from the abstracts to the publisher website and display the PDF copy on our platform. Clicks to view the full text will be directed to the publisher website, where only users with subscriptions or access through their institution are able to view the full article.