Enantioselective total syntheses of belactosin A, belactosin C, and its homoanalogue.
[reaction: see text] Enantioselective total syntheses of belactosin A, belactosin C, and its homoanalogue have been accomplished in high overall yields (32% for belactosin A from the amino acid 10, and 35 and 36% for belactosin C and its homoanalogue, respectively). This concise approach comprises a novel sequential acylation/beta-lactonization reaction and allows a facile alteration of the substituents, thus providing a flexible route to a new family of highly active belactosin-based proteasome inhibitors.
Larionov
Oleg V
OV
Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Goettingen, Germany.
de Meijere
Armin
A
D000215:Acylation; D004151:Dipeptides / Q000138:chemical synthesis*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D036341:Intercellular Signaling Peptides and Proteins; D007783:Lactones / Q000138:chemical synthesis; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis*; D061988:Proteasome Inhibitors; D013237:Stereoisomerism
D004151:Dipeptides; D004791:Enzyme Inhibitors; D036341:Intercellular Signaling Peptides and Proteins; D007783:Lactones; D010455:Peptides; D061988:Proteasome Inhibitors; C406052:belactosin A; C406053:belactosin B; C406054:belactosin C