Synthesis of a TMC-95A ketomethylene analogue by cyclization via intramolecular Suzuki coupling.
[structure: see text] A TMC-95A analogue extended at the C-terminus with NlePsi[COCH(2)]Gly-Ala-Ala-NH(2) was synthesized via side-chain cyclization of the linear precursor by a Suzuki cross-coupling reaction in solution to analyze the effect of additional P' residues on the inhibitory potency against yeast proteasome.
Kaiser
Markus
M
Max-Planck-Institut für Biochemie, AG Bioorganische Chemie, 82152 Martinsried, Germany.
Siciliano
Carlo
C
Assfalg-Machleidt
Irmgard
I
Groll
Michael
M
Milbradt
Alexander G
AG
Moroder
Luis
L
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis*; D003500:Cyclization; D003546:Cysteine Endopeptidases; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D007700:Kinetics; D015394:Molecular Structure; D009097:Multienzyme Complexes / Q000037:antagonists & inhibitors; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D046988:Proteasome Endopeptidase Complex; D013237:Stereoisomerism; D015003:Yeasts
D019086:Bridged Bicyclo Compounds, Heterocyclic; D004791:Enzyme Inhibitors; D009097:Multienzyme Complexes; D010456:Peptides, Cyclic; C408291:TMC-95A; D003546:Cysteine Endopeptidases; D046988:Proteasome Endopeptidase Complex