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Merck
CN

A1341

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

≥90% (HPLC), powder

Synonym(s):

Ac-ESMD-CHO

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About This Item

Empirical Formula (Hill Notation):
C19H30N4O10S
CAS Number:
191338-87-1
Molecular Weight:
506.53
NACRES:
NA.77
PubChem Substance ID:
329770361
UNSPSC Code:
12352202
MDL number:
MFCD01318859
Assay:
≥90% (HPLC)
Form:
powder

Key Documents

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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

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 key

TVTYMGFOGZRIHG-XUXIUFHCSA-N

assay

≥90% (HPLC)

form

powder

color

white

solubility

H2O: 1 mg/mL

storage temp.

−20°C

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 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 Ki of approximately 1300 nM, which makes it a weaker inhibitor than other inhibitor tetrapeptide analogs.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
098H1195

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Dominique Le Goff et al.
Reproductive toxicology (Elmsford, N.Y.), 21(3), 329-334 (2005-11-02)
The aim of the present study was to determine whether or not apoptosis occurs in Sertoli cells in presence of 25-hydroxycholesterol, an oxysterol derived from cholesterol-containing foods or endogenous oxidation. Here, we provide evidence that 25-hydroxycholesterol can induce cultured Sertoli
Johnson Agniswamy et al.
The FEBS journal, 274(18), 4752-4765 (2007-08-19)
Many protein substrates of caspases are cleaved at noncanonical sites in comparison to the recognition motifs reported for the three caspase subgroups. To provide insight into the specificity and aid in the design of drugs to control cell death, crystal
Z Han et al.
The Journal of biological chemistry, 272(20), 13432-13436 (1997-05-16)
The apoptotic cysteine protease, caspase-3, is expressed in cells as an inactive 32-kDa precursor from which 17 kDa (p17) and 12 kDa (p12) subunits of the mature caspase-3 are proteolytically generated during apoptosis. Two amino acid sequences, ESMD downward arrowS

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