Diketopiperazines in peptide and combinatorial chemistry.
Diketopiperazines (DKPs), the smallest cyclic peptides, represent an important class of biologically active natural products and their research has been fundamental to many aspects of peptide chemistry. The advent of combinatorial chemistry has revived interest in DKPs for two reasons: firstly, they are simple heterocyclic scaffolds in which diversity can be introduced and stereochemically controlled at up to four positions; secondly, they can be prepared from readily available alpha-amino acids using very robust chemistry. Here synthetic methods, conformation, as well as applications of DKPs are summarized and discussed critically.
Fischer
Peter M
PM
Cyclacel Limited, Dundee, Scotland, UK. pfischer@cyclacel.com
D000596:Amino Acids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D054659:Diketopiperazines; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry*
D000596:Amino Acids; D054659:Diketopiperazines; D010455:Peptides; D010879:Piperazines