N,S-Diacetylcysteamine
N,S-Diacetylcysteamine is an N-acetylcysteamine thioester (SNAc) derivative that serves as an acetyl donor, substrate, substrate inhibitor, condensing agent, and acyl donor. N,S-Diacetylcysteamine acts as an acetyl donor in the INH (Isoniazid) (HY-B0329) acetylation reaction in rhesus monkey liver homogenate, functions as a substrate for pigeon liver arylamine acetylase, and exhibits substrate inhibition against both systems at excessively high concentrations. N,S-Diacetylcysteamine acts as a substrate for peptidoglycan O-acetyltransferase B (PatB) to mediate the acetylation modification of peptidoglycan, and serves as a thioester model for the thioester groups of acetyl-CoA and acyl carrier protein.
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- CAS No.: 1420-88-8
- Formula: C6H11NO2S
- Molecular Weight:161.22
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Storage:
Please store the product under the recommended conditions in the Certificate of Analysis.
Biological Activity
N,S-Diacetylcysteamine (compound 6) is efficiently used by purified PatB as an acetyl donor to modify the peptidoglycan mimic NAG, with optimal catalytic efficiency (kcat/Km = 1103 M-1s-1) at pH 8.5[1].
N,S-Diacetylcysteamine combined with PatB protects isolated peptidoglycan from Bacillus subtilis ΔOat, Escherichia coli, Pseudomonas putida, and Vibrio parahemolyticus against lysozyme degradation in vitro[1].
N,S-Diacetylcysteamine combined with PatB results in minimal fluorescent labeling of peptidoglycan in intact Bacillus subtilis ΔOat and wild-type cells, indicating low efficiency for whole-cell PG modification relative to alkynyl SNAc analogs[1].
N,S-Diacetylcysteamine acts as an acetyl-group donor for pigeon liver arylamine acetylase, with a Km of 300 × 10-4 M (with 5.8 × 10-3 M INH), and excessive concentrations inhibit the enzyme[2].
N,S-Diacetylcysteamine (0.001-0.50 M) undergoes carbon-carbon condensation with the carbanion forms of malononitrile (k2 = 88 M-1 min-1), N-acetyl-S-cyanoacetylcysteamine (k2 = 0.084 M-1 min-1), and ethyl cyanoacetate (k2 = 3.0 M-1 min-1) in aqueous solution at 25°C and 1 M ionic strength, forming acetylated carbanion products and N-acetylcysteamine[4].
N,S-Diacetylcysteamine (1.0×10-4 M; up to 200 minutes) has acetyl transfer to ethyl cyanoacetate catalyzed by imidazole in aqueous solution at 25°C and 1 M ionic strength, increasing the reaction rate by ~103-fold at 1 M imidazole and pH 7, with product yields decreasing as imidazole concentration increases[4].
N,S-diacetylcysteamine (0.17 mM) undergoes hydroxide-catalyzed hydrolysis in aqueous solution at 25°C and 1 M ionic strength with a second-order rate constant of 9.1 M-1 min-1[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 1420-88-8
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Molecular Weight 161.22
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Formula C6H11NO2S
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SMILES
O=C(C)SCCNC(C)=O
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Purity & Documentation
References
[1]. Wang Y, et al. Postsynthetic Modification of Bacterial Peptidoglycan Using Bioorthogonal N-Acetylcysteamine Analogs and Peptidoglycan O-Acetyltransferase B. Journal of the American Chemical Society. 2017 Oct 04;139(39):13596-13599. [Content Brief]
[2]. Goedde HW, et al. Individual different response to drugs: characterisation of an INH-acetylating system in rhesus monkeys. Biochem Pharmacol. 1967 Sep 9;16(9):1793-9. [Content Brief]
[3]. Weber AL, et al. Formation of pyrophosphate, tripolyphosphate, and phosphorylimidazole with the thioester, n, s-diacetyl-cysteamine, as the condensing agent. Journal of molecular evolution. 1981;18(1):24-9. [Content Brief]
Calculators
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)