Diversity-oriented approaches to unusual α-amino acids and peptides: step economy, atom economy, redox economy, and beyond.
Here we describe several useful strategies to a variety of unusual α-amino acid derivatives and peptides based on "building block" approach. These building blocks are suitable for modification at an amino acid as well as at a peptide level. Moreover, these methods have embedded several points for diversification and are capable of producing a library of modified amino acids and peptides. We have employed highly atom-economic processes such as the Diels-Alder reaction, [2 + 2 + 2] cycloaddition, Suzuki-Miyaura cross-coupling, and olefin metathesis as key steps to assemble various unnatural amino acid derivatives and peptides. In some instances, we have used rongalite to generate Diels-Alder precursors.
Department of Chemistry, Indian Institute of Technology Bombay Powai, Mumbai 400 076, India.
Sambasivarao
S
Kotha
Deepti
D
Goyal
Arjun S
AS
Chavan
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D019151:Peptide Library; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
D000596:Amino Acids; D019151:Peptide Library; D010455:Peptides