Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Preorganized Cyclic α,α-Disubstituted α-Amino Acids Bearing Functionalized Side Chains That Act as Peptide-Helix Inducers

Preorganized Cyclic α,α-Disubstituted α-Amino Acids Bearing Functionalized Side Chains That Act as Peptide-Helix Inducers
Hiroyuki Kobayashi, Yosuke Demizu, Kenji Matsuno, Takashi Misawa
Preorganized cyclic α,α-disubstituted α-amino acids (dAA) bearing functionalized side chains that acted as peptide-helix inducers, which could be used for solid-phase peptide synthesis, were designed and synthesized. Furthermore, a helical octapeptide with the following amino acid sequence was prepared, and its preferred conformation was analyzed based on its CD spectra: Ac-X1EYSAX2KA-NH2 (11: X1 = ApiC4N3, X2 = Ac6c). The side-chain azido functional group of peptide 11 was efficiently converted to various 1,2,3-triazole groups via Huisgen 1,3-dipolar cycloaddition reactions involving different types of alkynes. The new cyclic dAA derivatives, which combine the advantages of conformational preorganization and side-chain functional groups, should prove to be a useful tool for the further development of biologically active peptides.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01946

DOI: 10.1021/acs.joc.7b01946

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.