File:L-Histidin_-_L-Histidine.svg · Wikimedia Commons · See Wikimedia Commons
L-histidine
Sign in to saveAlso known as L-His, (S)-4-(2-Amino-2-carboxyethyl)imidazole, (S)-a-Amino-1H-imidazole-4-propanoic acid, (S)-alpha-amino-1H-Imidazole-4-propanoic acid, (S)-alpha-Amino-1H-imidazole-4-propionic acid, (S)-α-amino-1H-Imidazole-4-propanoic acid, H, His
thumb|Histidine ball and stick model spinning Histidine or histidin (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –NH3+ form under biological conditions), a carboxylic acid group (which is in the deprotonated –COO− form under biological conditions), and an imidazole side chain (which is partially protonated), classifying it as a positively charged amino acid at physiological pH. Initially thought essential only for infants, it has now been shown in longer-term studies to be essential for adult
L-histidine is an essential amino acid, meaning your body needs it to build proteins but cannot produce it on its own, so you must obtain it from food. It has a unique chemical structure with a positively charged side chain that allows it to play important roles in protein function, and while once thought necessary only for infants, research has shown it remains essential for adults as well.
AI-generated from the Wikipedia summary — may contain errors.
Chemical data
- Formula
- C6H9N3O2
- Molecular weight
- 155.15 g/mol
- IUPAC name
- (2S)-2-azaniumyl-3-(1H-imidazol-5-yl)propanoate
- SMILES
- C1=C(NC=N1)C[C@@H](C(=O)[O-])[NH3+]
- InChIKey
- HNDVDQJCIGZPNO-YFKPBYRVSA-N
- XLogP
- -2.6
- Polar surface area
- 96.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
61,702 papers- l-Histidine Supplementation in Adults and Young Children with Atopic Dermatitis (Eczema).ReviewThe Journal of nutrition · 2020Gibbs NKDOI: 10.1093/jn/nxaa200
- Intelligent poly(l-histidine)-based nanovehicles for controlled drug delivery.ReviewJournal of controlled release : official journal of the Controlled Release Society · 2022Zhang Y, Kim I, Lu Y et al.DOI: 10.1016/j.jconrel.2022.08.005
- The self-assembly of L-histidine might be the cause of histidinemia.Scientific reports · 2023Ajikumar A, Premkumar AKN, Narayanan SPDOI: 10.1038/s41598-023-44749-5
- L-Histidine attenuates NEFA-induced inflammatory responses by suppressing Gab2 expression.Life sciences · 2024Li M, Wang H, Ren H et al.DOI: 10.1016/j.lfs.2024.122672
- L-Histidine Modulates the Catalytic Activity and Conformational Changes of the HD3 Deoxyribozyme.Genes · 2024Sakimoto N, Imanaka H, Tomita-Sudo E et al.DOI: 10.3390/genes15111481
- L-histidine inhibits the heat-induced gelation of actomyosin in a low ionic strength solution.Animal science journal = Nihon chikusan Gakkaiho · 2023Hayakawa T, Kubono Y, Fujii S et al.DOI: 10.1111/asj.13825
- Biosynthesis of l-histidine from marine biomass-derived galactans in metabolically engineered Corynebacterium glutamicum.Bioresource technology · 2024Kim M, Oh JW, Jeong DW et al.DOI: 10.1016/j.biortech.2023.129963
- Highly Efficient Production of l-Histidine from Glucose by Metabolically Engineered Escherichia coli.ACS synthetic biology · 2020Wu H, Tian D, Fan X et al.DOI: 10.1021/acssynbio.0c00163
via PubMed
~13 min read
Encyclopedic overview
12 sectionsContents
- Properties of the imidazole side chain
- Ligand
- Metabolism
- Biosynthesis
- Regulation of biosynthesis
- Degradation
- Conversion to other biologically active amines
- Requirements
- Medical uses
- See also
- References
- External links
thumb|Histidine ball and stick model spinning Histidine or histidin (symbol His or H) is an essential amino acid that is used in the biosynthesis of proteins. It contains an α-amino group (which is in the protonated –NH3+ form under biological conditions), a carboxylic acid group (which is in the deprotonated –COO− form under biological conditions), and an imidazole side chain (which is partially protonated), classifying it as a positively charged amino acid at physiological pH. Initially thought essential only for infants, it has now been shown in longer-term studies to be essential for adults also. It is encoded by the codons CAU and CAC.
Histidine was first isolated by Albrecht Kossel and Sven Gustaf Hedin in 1896. The name stems from its discovery in tissue, from histós "tissue". It is also a precursor to histamine, a vital inflammatory agent in immune responses. The acyl radical is histidyl.
Excerpted from Wikipedia’s “L-histidine” article, available under the CC BY-SA 4.0 licence.
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