Anserine

Anserine, a methylated dipeptide of β-alanine and 1-methylhistidine, serves as an endogenous antioxidant and pH-buffering model. The imidazole ring participates in proton shuttling and metal coordination. Researchers study its redox cycling, radical-scavenging, and chelation behavior in biochemical systems. Applications include muscle-metabolism research, food biochemistry, and peptide-based antioxidant design.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Anserine(CAS 584-85-0)

CAT No: R2691

CAS No:584-85-0

Synonyms/Alias:ANSERINE;L-Anserine;584-85-0;N-beta-Alanyl-3-methyl-L-histidine;HDQ4N37UGV;CHEBI:18323;(2S)-2-(3-aminopropanoylamino)-3-(3-methylimidazol-4-yl)propanoic acid;beta-Alanyl-N(pai)-methyl-L-histidine;Na-(3-aminopropanoyl)-Np-methyl-L-histidine;MFCD11040910;(2~{S})-2-(3-azanylpropanoylamino)-3-(3-methylimidazol-4-yl)propanoic acid;(S)-2-(3-Aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid;L-Histidine, N-beta-alanyl-3-methyl-;UNII-HDQ4N37UGV;EINECS 209-545-0;beta-Alanyl-N(pi)-methyl-L-histidine;Anserine [WHO-DD];(2S)-2-[(3-ammoniopropanoyl)amino]-3-(1-methyl-1H-imidazol-5-yl)propanoate;ANSERINE [MI];SCHEMBL34255;H-beta-Ala-His(3-Me)-OH;H-?-Ala-His(3-Me)-OH;CHEMBL448301;DTXSID30973950;L-N-b-alanyl-3-methyl-Histidine;N-b-alanyl-3-methyl-L-Histidine;L-N-beta-alanyl-3-methyl-Histidine;s6141;AKOS015896389;FA34800;AS-19301;HY-113354;CS-0062279;NS00015140;L-HISTIDINE, .BETA.-ALANYL-3-METHYL-;C01262;I11595;L-HISTIDINE, N-.BETA.-ALANYL-3-METHYL-;N(alpha)-(beta-alanyl)-N(pros)-methylhistidine;Q415335;HISTIDINE, N-.BETA.-ALANYL-3-METHYL-, L-;(2S)-2-(3-aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid;(S)-2-(3-Aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoicacid;8V3;

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M.F/Formula
C10H16N4O3
M.W/Mr.
240.26
Sequence
Three Letter Code:H-bAla-His(3-Me)-OH

Anserine, also known as β-alanyl-1-methyl-L-histidine, is a naturally occurring dipeptide found predominantly in the skeletal muscle and brain tissues of various animals, especially in fish and poultry. Recognized for its unique biochemical properties, Anserine has garnered significant attention in the fields of biochemistry and nutritional science. Structurally, it is closely related to carnosine, sharing similar antioxidant and pH-buffering capabilities, which make it a valuable subject for research and industrial applications. Its stability under physiological conditions and its ability to interact with reactive oxygen species have led to extensive studies exploring its potential benefits and mechanisms of action. The presence of Anserine in dietary sources has also sparked interest in its role in human nutrition and metabolism, further expanding its relevance across multiple scientific disciplines.

Antioxidant Research: In the realm of antioxidant research, Anserine serves as a powerful model compound for investigating cellular defense mechanisms against oxidative stress. Researchers utilize it in in vitro and in vivo systems to elucidate how dipeptides can neutralize free radicals and protect biomolecules from oxidative damage. The dipeptide's ability to chelate transition metals and scavenge reactive oxygen species is particularly significant for studies focused on cellular aging, neuroprotection, and the mitigation of oxidative damage in metabolic tissues. By incorporating Anserine into experimental models, scientists are able to dissect the pathways involved in endogenous antioxidant defense and explore novel therapeutic strategies for managing oxidative stress-related disorders.

Food Science and Nutritional Studies: Within food science, Anserine is frequently analyzed for its role as a functional ingredient in animal-derived foods. Its presence in muscle tissues of fish and poultry is a key factor in the nutritional evaluation of these foods, contributing to the overall antioxidant capacity and buffering properties. Food technologists and nutritionists investigate how dietary intake of this dipeptide may influence muscle performance, fatigue resistance, and general health outcomes. Moreover, Anserine's stability during food processing and its interactions with other bioactive compounds are critical for developing value-added food products and optimizing dietary recommendations for various populations.

Sports and Exercise Physiology: In sports and exercise physiology, Anserine is utilized as a research tool to examine muscle performance, endurance, and recovery. Its role as a pH buffer within muscle cells allows for the study of mechanisms underlying fatigue and lactic acid accumulation during intense physical activity. By supplementing experimental diets or using it as a biomarker in tissue analysis, exercise scientists can better understand how dipeptides like this one contribute to enhanced athletic performance and muscle recovery. These insights aid in the formulation of targeted nutritional strategies for athletes and physically active individuals.

Comparative Physiology and Evolutionary Biology: The distribution of Anserine across different animal species provides a unique perspective for studies in comparative physiology and evolutionary biology. Researchers compare its concentrations in various tissues to investigate adaptive strategies for coping with environmental stressors, such as hypoxia or temperature fluctuations. The evolutionary significance of dipeptide accumulation in certain species informs our understanding of metabolic adaptation and resilience. This comparative approach not only sheds light on the functional diversity of bioactive peptides but also guides the exploration of new sources and analogs with potential biotechnological applications.

Analytical Biochemistry and Biomarker Discovery: Analytical biochemists employ Anserine as a reference compound in the development and validation of chromatographic and spectrometric methods. Its quantification in biological samples is essential for biomarker discovery, particularly in studies assessing dietary intake, muscle metabolism, and physiological status. Accurate measurement of this dipeptide enables researchers to monitor metabolic changes, assess nutritional interventions, and explore its potential as a diagnostic indicator in various research settings. The development of sensitive and specific analytical techniques for Anserine detection continues to advance the fields of metabolomics and nutritional biochemistry, supporting a wide range of scientific investigations.

InChI
InChI=1S/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1
InChI Key
MYYIAHXIVFADCU-QMMMGPOBSA-N

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