1228687-82-8

Basic information

• Product Name: C₂₆H₄₃N₃O₅
• CAS NO: 1228687-82-8
• Molecular Weight: 477.645
• Mol File: 1228687-82-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₂₆H₄₃N₃O₅(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₆H₄₃N₃O₅(1228687-82-8)
• EPA Substance Registry System: C₂₆H₄₃N₃O₅(1228687-82-8)

Safety Data

• Hazardous Substances Data: 1228687-82-8(Hazardous Substances Data)

Downstream Products

• 1211877-43-8 Cbz-D-leu-L-leu-D-leu-H 

Relevant articles and documents

Studies of the synthesis of all stereoisomers of MG-132 proteasome inhibitors in the tumor targeting approach

MG-132 is a tripeptide aldehyde (Z-L-leu-L-leu-L-leu-H, 2) proteasome inhibitor that exerts antitumor activity and enhances cytostatic/cytotoxic effects of chemo- and radiotherapy. Because of a troublesome synthesis of tripeptides with a non-natural configuration and modified side chains of amino acids, only two stereoisomers of MG-132 have been reported. Here, we propose a new approach to the synthesis of tripeptide aldehydes based on the Ugi reaction. Chiral, enantiomerically stable 2-isocyano-4-methylpentyl acetates were used as substrates for Ugi reaction resulting in a formation of tripeptide skeletons. Further functionalization of the obtained products led to a synthesis of tripeptide aldehydes. All stereoisomers of MG-132 were synthesized and studied as potential inhibitors of chymotrypsin-like, trypsin-like, and peptidylglutamyl peptide hydrolyzing activities of proteasome. These studies demonstrated the influence of absolute configuration of chiral aldehydes on the cytostatic/cytotoxic effects of the synthesized compounds and revealed that only (S,R,S)-(-)-2 stereoisomer is a more potent. proteasome inhibitor than MG-132.