WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 593146
CAS#: 1027141-02-1
Description: Z-VAE(OMe)-fmk is a cell-permeable and irreversible UCHL1 inhibitor. The inhibitor approaches the active-site cleft from the opposite side of the crossover loop as compared to the direction of approach of ubiquitin's C-terminal tail, thereby occupying the P1' (leaving group) site, a binding site perhaps used by the unknown C-terminal extension of ubiquitin in the actual in vivo substrate(s) of UCHL1.
MedKoo Cat#: 593146
Name: Z-VAE(OMe)-fmk
CAS#: 1027141-02-1
Chemical Formula: C23H32FN3O7
Exact Mass: 481.2224
Molecular Weight: 481.5214
Elemental Analysis: C, 57.37; H, 6.70; F, 3.95; N, 8.73; O, 23.26
This product is not in stock, which may be available by custom synthesis.
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Synonym: Z-VAE(OMe)-fmk; ZVAE(OMe) fmk; ZVAE(OMe)fmk;
IUPAC/Chemical Name: L-Alaninamide, N-[(phenylmethoxy)carbonyl]-L-valyl-N-[(1S)-1-(2-fluoroacetyl)-4-methoxy-4-oxobutyl]-
InChi Key: MQWWOZGUKREVHO-KNBMTAEXSA-N
InChi Code: InChI=1S/C23H32FN3O7/c1-14(2)20(26-23(32)34-13-16-8-6-5-7-9-16)22(31)27(15(3)21(25)30)17(18(28)12-24)10-11-19(29)33-4/h5-9,14-15,17,20H,10-13H2,1-4H3,(H2,25,30)(H,26,32)/t15-,17-,20-/m0/s1
SMILES Code: C[C@@H](C(N)=O)N(C([C@H](C(C)C)NC(OCC1=CC=CC=C1)=O)=O)[C@H](C(CF)=O)CCC(OC)=O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 481.5214 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Davies CW, Chaney J, Korbel G, Ringe D, Petsko GA, Ploegh H, Das C. The co-crystal structure of ubiquitin carboxy-terminal hydrolase L1 (UCHL1) with a tripeptide fluoromethyl ketone (Z-VAE(OMe)-FMK). Bioorg Med Chem Lett. 2012 Jun 15;22(12):3900-4. doi: 10.1016/j.bmcl.2012.04.124. Epub 2012 May 4. PubMed PMID: 22617491; PubMed Central PMCID: PMC3372403.
2: Nathan J. SchauerRobert S. MaginXiaoxi LiuLaura M. DohertySara J. Buhrlage* Advances in Discovering Deubiquitinating Enzyme (DUB) Inhibitors. Journal of Medicinal Chemistry, Articles ASAP (Perspective). Publication Date (Web):November 4, 2019DOI: 10.1021/acs.jmedchem.9b01138.
