1027141-02-1
Chemical Structure
Z-VAE(OMe)-FMK
- CAS. Nr.: 1027141-02-1
- Formula:C23H32FN3O7
- Molecular Weight:481.52
IUPAC Name: methyl (5S,8S,11S)-11-(2-fluoroacetyl)-5-isopropyl-8-methyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazatetradecan-14-oate
InChIKey: VBAAQBLMAIONMC-KNBMTAEXSA-N
SMILES: [C@H](NC([C@@H](NC([C@@H](NC(OCC1=CC=CC=C1)=O)[C@H](C)C)=O)C)=O)(CCC(OC)=O)C(CF)=O
Biological Activity: Z-VAE (OMe)-FMK is a selective inhibitor of UCHL1, with better selectivity over UCHL3 and UCHL5. Z-VAE (OMe)-FMK binds to the active site cleft, covalently modifies the active site cysteine C90 to form a thioether bond, binds to inactive UCHL1 with a misaligned catalytic triad, and acts via a two-step addition-folding/migration/displacement mechanism. Z-VAE (OMe)-FMK stabilizes interactions through hydrogen bonding with oxyanion hole residues and van der Waals interactions with surrounding residues. Z-VAE (OMe)-FMK can be used in research related to colorectal cancer, lung cancer, pancreatic cancer, and Alzheimer's disease[1][2].
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Z-VAE(OMe)-FMK | Z-VAE (OMe)-FMK is a selective inhibitor of UCHL1, with better selectivity over UCHL3 and UCHL5. Z-VAE (OMe)-FMK binds to the active site cleft, covalently modifies the active site cysteine C90 to form a thioether bond, binds to inactive UCHL1 with a misaligned catalytic triad, and acts via a two-step addition-folding/migration/displacement mechanism. Z-VAE (OMe)-FMK stabilizes interactions through hydrogen bonding with oxyanion hole residues and van der Waals interactions with surrounding residues. Z-VAE (OMe)-FMK can be used in research related to colorectal cancer, lung cancer, pancreatic cancer, and Alzheimer's disease. | |||||||||||||||||||||
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References
- [1]. Davies CW, et al. The co-crystal structure of ubiquitin carboxy-terminal hydrolase L1 (UCHL1) with a tripeptide fluoromethyl ketone (Z-VAE(OMe)-FMK). Bioorganic & medicinal chemistry letters. 2012 Jun 15;22(12):3900-4. [Content Brief]
- [2]. Qin B, et al. DUBs in Alzheimer's disease: mechanisms and therapeutic implications. Cell death discovery. 2024 Nov 20;10(1):475.
