ISSN:
1434-193X
Keywords:
Amino acids
;
Enolates
;
Rearrangements
;
Metal complexes
;
Peptides
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
-Deprotonation of allylic esters of peptides at -70 °C in the presence of metal salts results in the formation of metal peptide enolate complexes, which undergo Claisen rearrangement on warming to room temperature to produce stereoselectively modified peptides. By far the best results are obtained with manganese enolates. With these enolates, the amino acids incorporated in the peptide chain have no significant influence on the rearrangement, neither on the yield nor on the stereochemical outcome. Therefore, this protocol is extremely suitable for the stereoselective modification of peptides by using esters of chiral allylic alcohols. α-Alkylated amino acids can be incorporated into peptides as well.
Additional Material:
2 Tab.
Type of Medium:
Electronic Resource