Optimized synthesis of hydrogen-bond surrogate helices: surprising effects of microwave heating on the activity of Grubbs catalysts.
This manuscript discusses microwave-assisted solid-phase synthesis of hydrogen-bond surrogate based alpha-helices and analogues by ring-closing metathesis (RCM). Microwave-mediated RCM allows access to a greater variety of amino acid residues in the macrocycles in shorter reaction times and higher yields compared to conventional heating. Surprisingly, we discovered that the Grubbs II catalyst is highly active under the influence of microwaves but catalytically dead under oil-bath conditions for the metathesis of these peptide bisolefins. [reaction: see text]
Chapman
Ross N
RN
Department of Chemistry, New York University, 100 Washington Square East, New York, NY 10003, USA.
Arora
Paramjit S
PS
D000475:Alkenes / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D006358:Hot Temperature; D006860:Hydrogen Bonding; D008872:Microwaves; D010455:Peptides / Q000138:chemical synthesis; D011487:Protein Conformation; D017433:Protein Structure, Secondary; D012997:Solvents
D000475:Alkenes; D000596:Amino Acids; D010455:Peptides; D012997:Solvents