A1341

N-Acetyl-Glu-Ser-Met-Asp-al

≥90% (HPLC), powder

• Synonym(s): Ac-ESMD-CHO
• Empirical Formula (Hill Notation): C₁₉H₃₀N₄O₁₀S
• CAS Number: 191338-87-1
• Molecular Weight: 506.53
• MDL number: MFCD01318859
• UNSPSC Code: 12352202
• PubChem Substance ID: 329770361
• NACRES: NA.77

Properties

• assay: ≥90% (HPLC)
• form: powder
• color: white
• solubility: H₂O: 1 mg/mL
• storage temp.: −20°C
• SMILES string: CSCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(C)=O)C(=O)N[C@@H](CC(O)=O)C=O
• InChI: 1S/C19H30N4O10S/c1-10(26)20-12(3-4-15(27)28)18(32)23-14(9-25)19(33)22-13(5-6-34-2)17(31)21-11(8-24)7-16(29)30/h8,11-14,25H,3-7,9H2,1-2H3,(H,20,26)(H,21,31)(H,22,33)(H,23,32)(H,27,28)(H,29,30)/t11-,12-,13-,14-/m0/s1
• InChI key: TVTYMGFOGZRIHG-XUXIUFHCSA-N

Description

General description

N-Acetyl-Glu-Ser-Met-Asp-aldehyde (Ac-ESMD-CHO) is a tetrapeptide analog that act to inhibit the activity of caspase-3 and caspase-7 proteins, which are involved in apoptosis. Ac-ESMD-CHO has been shown to block formation of the caspase-3 p17 and p12 subunits, induce accumulation of the p20 precursor peptide, inhibit 25-hydroxycholesterol-induced apoptosis in rat Sertoli cells[1] and also to bind caspase-7.

Biochem/physiol Actions

In the caspase-3 precursor, procaspase-3, the ESMD amino acid sequence has been identified as a cleavage site for producing the p17 and p12 subunits of mature caspase 3; Ac-ESMD-CHO has been shown to inhibit the protease that cleaves procaspase-3 at this site. Ac-ESMD-CHO binds caspase-7 and inhibits with a K_i of approximately 1300 nM, which makes it a weaker inhibitor than other inhibitor tetrapeptide analogs[2].

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)