Creating carbon-carbon bonds with samarium diiodide for the synthesis of modified amino acids and peptides.
In this perspective, an overview of our experiences on the application of samarium diiodide in organic synthesis for the preparation of amino acid and peptide analogues is presented. Three different carbon-carbon bond forming reactions are discussed, including side chain introductions, gamma-amino acid synthesis and acyl-like radical additions for the construction of C-C mimics of the peptidic bonds.
Ebran
Jean-Philippe
JP
Center for Insoluble Proteins Structures, Department of Chemistry, Interdisciplinary Nanoscience Center, University of Aarhus, 8000, Aarhus C, Denmark.
Jensen
Christina M
CM
Johannesen
Sine A
SA
Karaffa
Jakob
J
Lindsay
Karl B
KB
Taaning
Rolf
R
Skrydstrup
Troels
T
D000478:Alkylation; D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D005650:Fumarates / Q000138:chemical synthesis / Q000737:chemistry; D005998:Glycine / Q000737:chemistry; D006031:Glycosylation; D007454:Iodides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D012493:Samarium / Q000737:chemistry*
D000577:Amides; D000596:Amino Acids; D004952:Esters; D005650:Fumarates; D007454:Iodides; D007659:Ketones; D010455:Peptides; D012493:Samarium; C446481:aliskiren; D002244:Carbon; C409809:samarium diiodide; D009584:Nitrogen; D005998:Glycine