Epimerization-free block synthesis of peptides from thioacids and amines with the Sanger and Mukaiyama reagents.
Highly activated thioesters formed by the rapid reaction of C-terminal thioacids derived from protected amino acids and peptides with the Sanger reagent and other electron-deficient aryl halides in the presence of a free amine immediately form a peptide bond with the amine. This essentially epimerization-free method was used for the 4+4 block synthesis of a hindered octapeptide (see scheme; Boc, Pbf, and Trt are protecting groups).
Crich
David
D
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, MI 48202, USA. dcrich@icsn.cnrs-gif.fr
Sharma
Indrajeet
I
D000588:Amines / Q000737:chemistry*; D000595:Amino Acid Sequence; D000596:Amino Acids / Q000737:chemistry; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013457:Sulfur Compounds / Q000737:chemistry
D000588:Amines; D000596:Amino Acids; D010455:Peptides; D013438:Sulfhydryl Compounds; D013457:Sulfur Compounds; C005732:thioacetic acid