10.07.2015 Views

Proceedings book download - 5Z.com

Proceedings book download - 5Z.com

Proceedings book download - 5Z.com

SHOW MORE
SHOW LESS

You also want an ePaper? Increase the reach of your titles

YUMPU automatically turns print PDFs into web optimized ePapers that Google loves.

H 2NSOONHHHNONOONHHHNNOOOONHHHNNOOONHOHHNNOOO ONHHHNONOONH 2Fig. 3. Structure of the pentamer functionalized with thedienophile <strong>com</strong>pound “Reppe anhydride”.H 2NSONHSOHHNNOONHOHHCRQIKIWFQNRRMKKWKKNNOOONHNOO ONNHFig. 4. “Reppe anhydride” pentamer connected via adisulfide bridge with the CPP.OHHNOHHNOOOONHHHNONOONH 2Fig. 5. Ligation product of the pentamer after the<strong>com</strong>plete DAR inv reaction with the diene <strong>com</strong>poundderivatized with the fluorescence marker dansyl chloride.Figure 5 shows the <strong>com</strong>plexmolecule after the <strong>com</strong>pleteligation by the DAR inv(shortened to the reactionsite). The steps of thechemical reaction aredocumented in detail byWiessler [2].Figure 5 also shows thereaction product of DAR inv -mediated ligation of theReppe anhydride pentamerwith the diaryl-1,2,4,5-tetrazine-3,6-dicarboxylatefunctionalized with twodansyl chloride dyes.Here we demonstratedthe design of PNA backbonebuilding blocks suitable fora multi-faced spectrum ofligation reactions. TheDAR inv is chemicallyfavourable [2, 5, 6].For future applicationsthe rapid and selectiveligation must also fulfillstrict requirements - e.g. 1)stable educts, and 2) properintermediates and products.To meet these demands, thePNA’s amide backbone canbe considered as anappropriate candidate. Thephysico-chemical propertieswarrant the intensive developmentof amide backbonebased molecules with allnew functions qualified forligation reactions in the fieldof the “Click chemistry”.References1. Waldeck, W., et al. Int. J. Med. Sci. 5, 273 (2008).2. Wiessler, M., Waldeck, W., Kliem, C., Pipkorn, R., Braun, K. Int. J. Med. Sci. 7, 19 (2009).3. Braun, K., et al. Int. J. Med. Sci. 7, 136 (2010).4. Wiessler, M., et al. Int. J. Med. Sci. 7, 213 (2010).5. Pipkorn, R., et al. J. Pept. Sci. 15, 235 (2009).6. Pipkorn, R., Wiessler, M., Waldeck, W., Braun, K. Biopolymers 92, 350 (2009).207

Hooray! Your file is uploaded and ready to be published.

Saved successfully!

Ooh no, something went wrong!