Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Cyclic Antifreeze Glycopeptide and Glycopeptoids and Their Ice Recrystallization Inhibition Activity

  • Ahn, Mija (Division of Magnetic Resonance, Korea Basic Science Institute) ;
  • Murugan, Ravichandran N. (Division of Magnetic Resonance, Korea Basic Science Institute) ;
  • Shin, Song Yub (Department of Bio-Materials, Graduate School and Department of Cellular & Molecular Medicine, School of Medicine, Chosun University) ;
  • Kim, Eunjung (Division of Polar Life Sciences, Korea Polar Research Institute) ;
  • Lee, Jun Hyuck (Division of Polar Life Sciences, Korea Polar Research Institute) ;
  • Kim, Hak Jun (Division of Polar Life Sciences, Korea Polar Research Institute) ;
  • Bang, Jeong Kyu (Division of Magnetic Resonance, Korea Basic Science Institute)
  • Received : 2012.07.26
  • Accepted : 2012.08.13
  • Published : 2012.11.20
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Abstract

Until now, few groups reported the antifreeze activity of cyclic glycopeptides; however, the tedious synthetic procedure is not amenable to study the intensive structure activity relationship. A series of N-linked cyclic glycopeptoids and glycopeptide have been prepared to evaluate antifreeze activity as a function of peptide backbone cyclization and methyl stereochemical effect on the rigid Thr position. This study has combined the cyclization protocol with solid phase peptide synthesis and obtained significant quantities of homogeneous cyclic glycopeptide and glycopeptoids. Analysis of antifreeze activity revealed that our cyclic peptide demonstrated RI activity while cyclic glycopeptoids showed no RI activity. These results suggest that the subtle changes in conformation and Thr orientation dramatically influence RI activity of N-linked glycopeptoids.

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References

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