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Cat. No.: HY-W095697

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N-Acetylhistidine

N-Acetylhistidine is a compatible osmolyte in the brain, retina, and lens of poikilothermic vertebrates, and binds to E. coli HisJ with a K_d of 27 μM. N-Acetylhistidine participates in the regulatory volume decrease process under hypotonic stress, assists cells in restoring homeostatic volume, and acts as a gradient-driven molecular water pump, exerting a protective effect against hypotonic swelling. N-Acetylhistidine can be used in combination with glutamate to inhibit the cobalt-resistant postsynaptic component in the electroretinogram. N-Acetylhistidine reduces Ca²⁺-induced growth inhibition and restores cell growth. N-Acetylhistidine can be used in research related to cataracts, diabetic distal symmetric polyneuropathy, and stroke.

For research use only. We do not sell to patients.

CAS No.: 2497-02-1
Formula: C₈H₁₁N₃O₃
Molecular Weight:197.19

Storage:

Please store the product under the recommended conditions in the Certificate of Analysis.

Data Sheet (288 KB)

N-Acetylhistidine Chemical Structure

CAS No.: 2497-02-1

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Use of MCE Products

Strong Fluorescence Signal / Multi-Disciplinary Applications / High Fluorescence Specificity

Biological Activity
- Description
- In Vitro
Chemical Information
Purity & Documentation
References
Calculators
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Biological Activity

Description

All Endogenous Metabolite Isoforms :

In Vitro

Anti-cancerGlutamate Release or ReceptorsProtein/Amino Acid MetabolismOthers

Anti-cancer

N-Acetylhistidine (10 mM) reduces Ca²⁺-induced growth inhibition and restores the cell growth of mouse breast cancer FM3A cells to 70-80% of normal^[9].

Glutamate Release or Receptors

N-Acetylhistidine (10 mM; 1-10 min), when used together with glutamate, inhibits the cobalt-resistant postsynaptic component in the electroretinogram of the perfused toad (Bufo marinus) retina^[1].

Protein/Amino Acid Metabolism

N-Acetylhistidine (24 h) content is linearly correlated with external osmotic pressure, increasing under hyperosmotic conditions and decreasing under hypoosmotic conditions in cultured Atlantic salmon lenses^[3].
N-Acetylhistidine (24 h) efflux is stimulated by hypotonic exposure in cultured Atlantic salmon lenses^[3].

Others

N-acetyl-L-histidine binds to E. coli HisJ with a K_d of 27 µM at pH 7.0^[2].
N-acetyl-L-histidine binds and interacts with E. coli HisJ and increases its thermal stability to a T_m of 57.0 °C^[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Related Protocols :

Chemical Information

CAS No. 2497-02-1
Molecular Weight 197.19
Formula C₈H₁₁N₃O₃
SMILES

O=C(O)[C@H](CC1=CNC=N1)NC(C)=O
Structure Classification
- Ketones, Aldehydes, Acids
Initial Source
- Endogenous metabolite
- Human Gut Microbiota Metabolites
Shipping

Room temperature in continental US; may vary elsewhere.
Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Purity & Documentation

Select Batch:

Purity: 99.98%

Assay: 99.98%

ee.: 99.98%

Data Sheet (288 KB)
COA (2659 KB)
Elemental Analysis Report (2659 KB)
HNMR (2659 KB)
CNMR (2659 KB)
RP-HPLC (2659 KB)
NP-HPLC (2659 KB)
MS (2659 KB)
LCMS (2659 KB)
IR (2659 KB)
GC (2659 KB)
OR (2659 KB)
SDS-PAGE (2659 KB)
SEC-HPLC (2659 KB)
Other Report (2659 KB)
Handling Instructions (2659 KB)

References

[1]. Schwartz EA, et al. Synaptic transmission in amphibian retinae during conditions unfavourable for calcium entry into presynaptic terminals. The Journal of physiology. 1986 Jul;376:411-28.

[2]. Paul S, et al. Ligand binding specificity of the Escherichia coli periplasmic histidine binding protein, HisJ. Protein science : a publication of the Protein Society. 2017 Feb;26(2):268-279.

[3]. Rhodes JD, et al. N-acetylhistidine, a novel osmolyte in the lens of Atlantic salmon (Salmo salar L.). American journal of physiology. Regulatory, integrative and comparative physiology. 2010 Oct;299(4):R1075-81.

[4]. Razzano V, et al. Poly-histidine grafting leading to fishbone-like architectures. RSC advances. 2018 Feb 23;8(16):8638-8656.

[5]. Xu J, et al. Ultra-high performance liquid chromatography coupled to tandem mass spectrometry-based metabolomics study of diabetic distal symmetric polyneuropathy. Journal of diabetes investigation. 2023 Sep;14(9):1110-1120.

[6]. Baslow MH. Function of the N-acetyl-L-histidine system in the vertebrate eye: Evidence in support of a role as a molecular water pump. Journal of Molecular Neuroscience. 1998 Jun;10(3):193-208.

[7]. Ge Y, et al. Effects of highland barley β-glucan on gut microbiota composition and metabolism in vitro fermentation. Food Chemistry: X. 2025 Jan 1;25:102089.

[8]. Baslow MH, et al. N-acetyl-L-histidine, a Prominent Biomolecule in Brain and Eye of Poikilothermic Vertebrates. Biomolecules. 2015 Apr 24;5(2):635-46. [Content Brief]

[9]. Nakamura M, et al. Toxic acrolein production due to Ca(2+) influx by the NMDA receptor during stroke. Atherosclerosis. 2016 Jan;244:131-7.

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Help & FAQs

How should lyophilized recombinant proteins be reconstituted and stored?

1. Before opening the cap, centrifuge the vial at 13000 rpm for 20-30 seconds. This step will ensure that any lyophilized powder that may have adhered to the cap or walls is collected at the bottom of the vial, minimizing the risk of product loss.

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100 mg

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