Totalsynthese des Antitumor-Wirkstoffes Berkelic Acid

• Applicant: Dr. Nicole Miller
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2007 to 2012
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 59451111

• Final Report Year: 2010

Final Report Abstract

Valuable α-GalNAc containing “Tn antigen mimic” have been synthesised and used as a building block in microwave-enhanced automated Fmoc-SPPS of analogues of AFGPs. In a second strategy, the neoglycoconjugation was performed on a multi-azido-functionalised peptide backbone, using only a catalytic quantity of Cu(I). Use of microwave irradiation enabled high-yielding and rapid syntheses of the neoglycopeptides providing a platform for the generation of a more extensive range of neoglycopeptides of biological relevance. The antifreeze activity of the synthesised peptides will be assessed to establish whether the sugar moiety tethered remotely from the peptide backbone via the triazole linker affords similar biological activity.

Publications

• Synthesis of Fish Antifreeze Neoglycopeptides Using Microwave-Assisted “Click Chemistry” Org. Lett. 2009, 11, 2409-2412
  Nicole Miller, Geoffrey M. Williams, Margaret A. Brimble