Synthesis of stapled beta3-peptides through ring-closing metathesis.
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.
Bergman
Ylva E
YE
School of Chemistry, Monash University, Clayton 3800 Victoria, Australia.
Del Borgo
Mark P
MP
Gopalan
Romila D
RD
Jalal
Sania
S
Unabia
Sharon E
SE
Ciampini
Marisa
M
Clayton
Daniel J
DJ
Fletcher
Jordan M
JM
Mulder
Roger J
RJ
Wilce
Jacqueline A
JA
Aguilar
Marie-Isabel
MI
Perlmutter
Patrick
P
D003500:Cyclization; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation; D017433:Protein Structure, Secondary
D010455:Peptides