Synthesis of Stapled β3-Peptides through Ring-Closing Metathesis Academic Article uri icon

abstract

  • The first synthesis of carbon-stapled beta(3)-peptides is reported. The precursor beta(3)-peptides, with O-allyl beta-serines located in an i/i+3 relationship, were prepared on solid phase. We show that efficient ring-closing metathesis (RCM) of these new beta(3)-peptides proceeds smoothly either in solution or on an appropriate solid support. All products were generated with high selectivity for the E-isomer.

authors

  • Bergman, Ylva E
  • Del Borgo, Mark P
  • Gopalan, Romila D
  • Jalal, Sania
  • Unabia, Sharon E
  • Ciampini, Marisa
  • Clayton, Daniel J
  • Fletcher, Jordan M
  • Mulder, Roger J
  • Wilce, Jacqueline A
  • Aguilar, Marie-Isabel
  • Perlmutter, Patrick

publication date

  • October 2009