Fas C- Terminal TripeptideAC-SER-LEU-VAL-OH CAS# 189109-90-8 |
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Quality Control & MSDS
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| Cas No. | 189109-90-8 | SDF | Download SDF |
| PubChem ID | 9209375 | Appearance | Powder |
| Formula | C16H29N3O6 | M.Wt | 359.42 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Ac-Ser-Leu-Val-OH | ||
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Sequence | Ac-Ser-Leu-Val-OH | ||
| Chemical Name | (2S)-2-[[(2S)-2-[[(2S)-2-acetamido-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoic acid | ||
| SMILES | CC(C)CC(C(=O)NC(C(C)C)C(=O)O)NC(=O)C(CO)NC(=O)C | ||
| Standard InChIKey | ORIIRLCDJGETQD-AVGNSLFASA-N | ||
| Standard InChI | InChI=1S/C16H29N3O6/c1-8(2)6-11(14(22)19-13(9(3)4)16(24)25)18-15(23)12(7-20)17-10(5)21/h8-9,11-13,20H,6-7H2,1-5H3,(H,17,21)(H,18,23)(H,19,22)(H,24,25)/t11-,12-,13-/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
Fas C- Terminal Tripeptide Dilution Calculator
Fas C- Terminal Tripeptide Molarity Calculator
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Fas C- Terminal Tripeptide,(C16H29N3O6), a tri-peptide with the sequence AC-SER-LEU-VAL-OH, it’s the C-terminal tripeptide of Fas, MW= 359.4. Fas (APO-1/CD95) is a cell surface receptor, which is a member of the tumor necrosis factor receptor (TNFR) superfamily, The Fas receptor is a death receptor on the surface of cells that leads to programmed cell death (apoptosis). It is one of two apoptosis pathways. Fas forms the death-inducing signaling complex (DISC) upon ligand binding. Upon ensuing death domain (DD) aggregation, the receptor complex is internalized via the cellular endosomal machinery. This allows the adaptor molecule FADD to bind the death domain of Fas through its own death domain. FADD also contains a death effector domain (DED) near its amino terminus,which facilitates binding to the DED of FADD-like interleukin-1 beta-converting enzyme (FLICE), more commonly referred to as caspase-8. FLICE can then self-activate through proteolytic cleavage into p10 and p18 subunits, two each of which form the active heterotetramer enzyme. Active caspase-8 is then released from the DISC into the cytosol, where it cleaves other effector caspases, eventually leading to DNA degradation, membrane blebbing, and other hallmarks of apoptosis.
The C-terminal tripeptide (AC-SER-LEU-VAL-OH) of Fas was necessary and sufficient both for binding to the third PDZ domain of FAP-1 and for inhibiting Fas/FAP-1 binding.
Figure1 Formula of Fas C- Terminal Tripeptide
Figure2 Signaling pathway of Fas
Ref:
1. Lichter P, Walczak H, Weitz S, Behrmann I, Krammer PH (September 1992). "The human APO-1 (APT) antigen maps to 10q23, a region that is syntenic with mouse chromosome 19". Genomics 14 (1): 179–80.
2. Inazawa J, Itoh N, Abe T, Nagata S (November 1992). "Assignment of the human Fas antigen gene (Fas) to 10q24.1". Genomics 14 (3): 821–2.
3. Huang B, et al. (1996). "NMR structure and mutagenesis of the Fas (APO-1/CD95) death domain". Nature 384 (6610): 638–41.
4. Eberstadt M, et al. (1998). "NMR structure and mutagenesis of the FADD (Mort1) death-effector domain". Nature 392 (6679): 941–5.
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Structural modification of Fas C-terminal tripeptide and its effects on the inhibitory activity of Fas/FAP-1 binding.[Pubmed:10464015]
J Med Chem. 1999 Aug 26;42(17):3289-99.
We report the structural requirements of the C-terminal tripeptide derivative of Fas (Ac-Ser-Leu-Val-OH, 1) for the inhibitory activity of Fas/FAP-1 binding. The presence of a carboxyl group and a L-Val residue at the C-terminus is essential for the inhibitory activity, and the hydroxyl group of Ser plays an important role as the donor of a hydrogen bond. The introduction of hydrophobic groups to the N-terminal region of 1, especially the phenylaminocarbonyl group (41), showed a remarkable increase in potency. Further improvement was observed by the attachment of the Glu residue to the meta-position of the phenyl ring of 41 (51). The ester derivative of 41 (56) had the ability to induce apoptosis which was dependent on the concentration of anti-Fas antibody in the colon cancer cell line, DLD-1, which expresses both Fas and FAP-1 and is resistant to Fas-induced apoptosis. We are now investigating whether FAP-1 is a main target of 56 and whether the inhibition of Fas/FAP-1 binding by 56 retrieves the apoptotic signal.
