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DL-Amino Acids
Catalog number
CAS number
Molecular Formula
Molecular Weight
2-amino-3-(1H-imidazol-5-yl)propanoic acid
Histidine; Histidine, DL-; DL-His-OH; (±)-Histidine; 1H-Imidazole-4-alanine; 2-Amino-3-(1H-imidazol-4-yl)propanoic acid; 2-Amino-3-(5-imidazolyl)propanoic acid
Related CAS
184709-11-3 (Deleted CAS) 351-50-8 (D-isomer) 71-00-1 (L-isomer)
Light pink powder
1.423±0.06 g/cm3
Melting Point
287°C (dec.)
Boiling Point
458.9±35.0°C at 760 Torr
Store at RT
InChI Key
Canonical SMILES
1.Research on the Terahertz Absorption Spectra of Histidine Enantiomer (L) and its Racemic Compound (DL)
Appl Spectrosc. 2017 Feb;71(2):194-202. doi: 10.1177/0003702816669728.
Terahertz time-domain spectroscopy (THz-TDS) is used to investigate the absorption spectra of polycrystalline L- and DL-histidine in the frequency range of 10-100 cm -1 . The spectra exhibit distinct differences in peak frequencies between the enantiomer (L-histidine) and racemic compound (DL-histidine). The observed spectral differences are attributed to the intermolecular interactions. With the density function theory (DFT) method, the frequencies of vibrational modes of L-histidine and DL-histidine in the THz range are calculated and well assigned according to the measured spectra. The origin of the observed vibrational modes is found to be non-localized and of a collective (phonon-like) nature, which points to the lattice and skeleton vibrations mediated by the hydrogen bond. Furthermore, we propose and demonstrate a method for determining the composition ratio of histidine mixtures based on the THz absorption spectra.
2.Histidine decarboxylase inhibitors: a novel therapeutic option for the treatment of leydigioma
J Endocrinol. 2022 Oct 3;255(3):103-116. doi: 10.1530/JOE-21-0419.
Recent reports indicate an increase in Leydig cell tumor (LCT) incidence. Radical orchiectomy is the standard therapy in children and adults, although it entails physical and psychosocial side effects. Testis-sparing surgery can be a consideration for benign LCT of 2.5 cm or less in size. Malignant LCTs respond poorly to conventional chemotherapy, so new treatment modalities are needed. In this study, we observed increased histidine decarboxylase expression and pro-angiogenic potential in LCT surgically resected from pediatric patients (fetal to pubertal) vs control samples from patients without endocrine or metabolic disorders which were collected at necropsy. We, therefore, evaluated for the first time the antitumor efficacy of two histidine decarboxylase inhibitors (α-methyl-dl-histidine dihydrochloride (α-MHD) and epigallocatechin gallate (EGCG)), alone and combined with carboplatin, in two preclinical models of LCT. MA-10 and R2C Leydig tumor cells, representing two different LCT subtypes, were used to generate syngeneic and xenograft mouse LCT models, respectively. In the syngeneic model, monotherapy with α-MHD effectively reduced tumor growth and angiogenesis. In the xenografts, which showed co-expression of histidine decarboxylase and CYP19, the combination of EGCG plus carboplatin was the most effective therapy, leading to LCT growth arrest and undetectable levels of plasmatic estradiol. Testicular and body weights remained unaltered. On the basis of this study, histidine decarboxylase may emerge as a novel pharmacological target for LCT treatment.
3.Histidine Self-assembly and Stability on Mineral Surfaces as a Model of Prebiotic Chemical Evolution: An Experimental and Computational Approach
Orig Life Evol Biosph. 2021 Jun;51(2):117-130. doi: 10.1007/s11084-021-09606-3.
The abiotic synthesis of histidine under experimental prebiotic conditions has proven to be chemically promising and plausible. Within this context, the present results suggest that histidine amino acid may function as a simple prebiotic catalyst able to enhance amino acid polymerization. This work describes an experimental and computational approach to the self-assembly and stabilization of DL-histidine on mineral surfaces using antigorite ((Mg, Fe) 3 Si 2 O 5 (OH) 4 ), pyrite (FeS 2 ), and aragonite (CaCO 3 ) as representative minerals of prebiotic scenarios, such as meteorites, and subaerial and submarine hydrothermal systems. Experimental results were obtained through polarized-light microscopy, IR spectroscopy (ATR-FTIR), and differential scanning calorimetry (DSC). Molecular dynamics was performed through computational simulations with the MM + method in HyperChem software. IR spectra suggest the presence of peptide bonds in the antigorite-histidine and aragonite-histidine assemblages with the presence of amide I and amide II vibration bands. The FTIR second derivative inspection supports this observation. Moreover, DSC data shows histidine stabilization in the presence of antigorite and aragonite by changes in histidine thermodynamic properties, particularly an increase in histidine decomposition temperature (272ºC in antigorite and 275ºC in aragonite). Results from molecular dynamics are consistent with DSC data, suggesting an antigorite-histidine closer interaction with decreased molecular distances (cca. 5.5 Å) between the amino acid and the crystal surface. On the whole, the experimental and computational outcomes support the role of mineral surfaces in prebiotic chemical evolution as enhancers of organic stability.
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