Pyrrole-based scaffolds for turn mimics.
Two amino acid derived synthons were combined to give homopropargylic amines 2. Platinum dichloride was used to cyclize these intermediates into pyrroles 3 which collapsed to the target secondary structure mimics 1 on treatment with base. Side chains of these compounds overlay with an idealized type 1 β-turn and with an inverse γ-turn.
Texas A & M University, Chemistry Department, College Station, Texas 77842, USA.
Eunhwa
E
Ko
Kevin
K
Burgess
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D057786:Peptidomimetics; D017433:Protein Structure, Secondary; D011758:Pyrroles / Q000737:chemistry*
D000588:Amines; D000596:Amino Acids; D057786:Peptidomimetics; D011758:Pyrroles
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