Disease relevance of histidine

• D-Histidine, imidazol and L-histidine methyl ester also elicited marked injury, while the N-substituted derivatives Nalpha-acetyl-L-histidine and tert-butyl-oxycarbonylhistidine and histidine-containing dipeptides showed almost no toxicity [1].
• D-histidine utilization in Salmonella typhimurium is controlled by the leucine-responsive regulatory protein (Lrp) [2].
• Synechocystis hemoglobin contains an unprecedented covalent bond between a nonaxial histidine side chain (H117) and the heme 2-vinyl [3].
• L-histidine but not D-histidine attenuates brain edema following cryogenic injury in rats [4].

Psychiatry related information on histidine

• D-Histidine, administered in the 'wthdrawal' phase of morphine addiction, failed to modify the expression of tolerance and physical dependence in mice [5].

High impact information on histidine

• This implies that there is a favourable interaction between the protonated form of His18 and the alpha-helix that should stabilize the native structure at neutral pH by 2.1 kcal mol-1 [6].
• The increase in stability of the enzyme as the pH changes from 8.5 to 6.3 is attributable to this interaction, and the pH-stability curve fits pKa values for His18 in native and urea-denatured enzymes that are consistent with the NMR data [6].
• The activation energy barriers for the transitions from the histidine-water coordinated form (HW) to the histidine-methionine coordinated form and the HH form are 18 and 4 kcal mol-1 respectively, at pH 4 [7].
• These results demonstrate that His704 is at the active site of neutral endopeptidase 24.11 and suggest a catalytic role for this residue [8].
• When placed into this active c-Raf mutant, mutation of W342 to D, K or H enabled phosphorylation and activation of the c-Raf substrate MEK at the plasma membrane but not in an immunoprecipitation assay [9].

Biological context of histidine

• Swapping the divergent histidine (H107) residue in GlyR alpha1, which together with the conserved H109 forms part of an intersubunit Zn2+-binding site, for the equivalent asparagine residue present in GlyR alpha2 and alpha3, reversed this phenotype [10].
• Occurrence of D-histidine residues in antimicrobial poly(arginyl-histidine), conferring resistance to enzymatic hydrolysis [11].
• Kinetics of D-histidine diffusion across rat intestine in vitro [12].

Anatomical context of histidine

• D-Histidine did not promote zinc uptake in either rat or human erythrocytes [13].
• The transport characteristics of L- and D-histidine through the blood-lung barrier were studied in cultured rat lung microvascular endothelial cells (LMECs) [14].
• Addition of L-histidine, and to a lesser extent D-histidine, to the culture media of U937 cells before LPS exposure, resulted in a significant dose-dependent reduction in LPS-induced intracellular DCF fluorescence, as measured quantitatively by flow cytometry [15].
• Results obtained proved that D-histidine transport in each direction (mucosa to seroa or seroa to mucosa) was dependent-concentration process [12].
• A five-compartment linear model for diffusion in vitro across rat jejunum has been proposed for the study of the kinetic constants of D-histidine transport [12].

Associations of histidine with other chemical compounds

• In both strains, responses to D-tryptophan and D-histidine significantly increased (167.7-216.7% of control) after the stimulation with Sac as compared with those applied before Sac [16].
• Closing this loop brings a negatively charged glutamate into the active site; this causes His448 to recruit a labile proton, which interacts favorably with Asp and accounts for most of the Asp/Asn discrimination [17].
• L-citrulline as well as D-histidine uptake is mediated solely by the general amino acid permease, and a gap1 strain is therefore able to grow in the presence of D-histidine but cannot utilize L-citrulline [18].
• Substance P analogues containing D-histidine antagonize the behavioural effects of intrathecally co-administered substance P in mice [19].
• The substitution of D-lysine for the N-terminal N-methyl-D-leucine does not seriously affect the in vitro antibacterial properties of the eremomycin aglycone whereas the heptapeptides with the N-terminal D-tryptophan or D-histidine moieties and the octapeptide with the N-terminal D-lysine are practically devoid of the antibacterial properties [20].

Gene context of histidine

• In general, the introduction of D-histidine in position 9 of the SP molecule resulted in potent antagonistic activity of the SP derivative on the behavioural responses to SP [19].
• These results provide evidence that His101 of gp91-phox is the one of the heme-binding ligands of cytochrome b558 [21].
• (1988, Gene 74, 365-373), we have constructed expression vectors which contain a sequence encoding six consecutive histidine residues (His6-tag) at the 3' end of the MBP-encoding malE gene which is followed by either a thrombin-binding site (LVPRGS) or a factor Xa-binding site (IEGR) [22].
• Further studies on heteromeric receptors demonstrated that a mutated beta subunit could indeed affect Zn2+-mediated inhibition but only from one side of the intersubunit Zn2+-binding site, equivalent to the GlyR alpha1 H107 face [10].
• While we have attributed the enhanced heterolysis to the electron donation from the thiolate ligand, possible participation of the distal histidine (H64, E7) in H93C Mb cannot be eliminated [23].

Analytical, diagnostic and therapeutic context of histidine

• From NMR titrations of wild-type and engineered mutants we find that the pKa of His18 is 7.9 in wild-type enzyme, 1.6 units above the value in the urea-denatured enzyme and in model peptides [6].
• Tryptic digestion of the radioactively labeled enzyme followed by high performance liquid chromatography allowed the isolation of a modified peptide with the sequence T-D-V-H-S-P-G-N-F-R in which histidine (His704) is the modified residue [8].

References