(S)-a-Amino-1H-imidazole-4-propanoic Acid/(S)-1H-Imidazole-4-alanine/a-Amino-4(or 5)-Imidazolepropionic Acid/d,l-histidine/1H-Imidazole-4-propanoic acid, α-amino-, (S)-/(S)-histidine/HISTIDINE, L-/His/Histidine/H-L-HIS-OH/3-(1H-imidazol-4-yl)-L-Alanine/hydrogen L-histidinate/L-His/Histidin/L-Histdine/L-Hisidine/L-Histidine/H-His-OH
458.9±35.0 °C at 760 mmHg
282 °C (dec.)(lit.)
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provides coniferyl ferulate(CAS#:71-00-1) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate
Galactose oxidase and amine oxidase contain a cofactor which is generated by post-translational chemical modification to the corresponding amino acid side chains near the copper active center. Such cofactors provide proteins unusual catalytic ability that canonical amino acids cannot exert as well as their structural stability, and thereby are called as protein-derived cofactors. These cofactors and modifications are mostly derived from aromatic amino acid residues, especially Tyr, Trp, and His. Current information about unusual cofactors derived from two of those, heteroaromatic residues (Trp and His) is summarized, especially chemical properties and maturation process of the cross-links between cysteine and heteroaromatic amino acids (His-Cys and Trp-Cys cross-links).Abbreviations: FMN: flavin mononucleotide; FAD: flavin adenine nucleotide; RNA: ribonucleic acid; PDC: protein-derived cofactor; GFP: green fluorescent protein; MIO: 3,5-dihydro-5-methylidene-4-imidazol-4-one; LTQ: lysyl tyrosylquinone; CTQ: cysteine tryptophylquinone; TTQ: tryptophan tryptophylquinone; E.coli: Escherichia coli; WT: wild type.
Posttranslational modifications; amine dehydrogenase; quinone cofactors; tyrosinase
His-Cys and Trp-Cys cross-links generated by post-translational chemical modification.
Naturally occurring fructosamines are of high clinical significance due to their potential use in diabetes mellitus monitoring (quantification of fructosylated hemoglobin, HbA1c) or for the investigation of their reactivity in consecutive reactions and harmfulness towards the organism. Here we report the specific synthesis of the fructosylated dipeptide L-valyl-L-histidine (Fru-Val-His) and fructosylated L-valine (Fru-Val). Both are basic tools for the development and validation of enzymatic HbA1c assays. The two fructosamine derivatives were synthesized via a protected glucosone intermediate which was coupled to the primary amine of Val or Val-His, performing a reductive amination reaction. Overall yields starting from fructose were 36% and 34% for Fru-Val and Fru-Val-His, respectively. Both compounds were achieved in purities > 90%. A HILIC-ESI-MS/MS method was developed for routine analysis of the synthesized fructosamines, including starting materials and intermediates. The presented method provides a well-defined and efficient synthesis protocol with purification steps and characterization of the desired products. The functionality of the fructosylated dipeptide has been thoroughly tested in an enzymatic HbA1c assay, showing its concentration-dependent oxidative degradation by fructosyl-peptide oxidases (FPOX). Graphical abstract.
Diabetes mellitus; FPOX assay; Fructosamines; Fructosylated hemoglobin; HILIC-ESI-MS/MS; HbA1c quantification
Direct glucosone-based synthesis and HILIC-ESI-MS/MS characterization of N-terminal fructosylated valine and valylhistidine for validation of enzymatic HbA1c assays in the diagnosis of diabetes mellitus.
Gerke C1,2, Buchholz M1, Muller H3, Meusinger R4, Grimmler M1,3, Metzmann E5.
We recently found that [Eu(pda)2 ]- (pda: 1,10-phenanthroline-2,9-dicarboxylic acid), which has an achiral structure in crystals, exhibits circularly polarized luminescence (CPL) in aqueous solutions containing chiral amino acids such as arginine and histidine. CPL measurements were performed for agar gel, which includes an aqueous solution of [Eu(pda)2 ]- and chiral arginine or histidine. The spectral shape, concentration, and pH dependences on CPL intensity in the agar gels were very close to those in aqueous solutions, indicating that the CPL of the EuIII complex in the agar gels was induced by mechanism similar to that in aqueous solutions. We performed spatially resolved CPL measurements using a laboratory-built microscopic CPL spectroscopic system for agar-gel samples, where d- and l- amino acids were separately dispersed. We successfully recorded CPL imaging maps showing spatial dispersions of d- and l-amino acid in the agar gels.
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
amino acid; chiral sensing; circularly polarized luminescence; fluorescence microscopy; lanthanide complex
Microscopic Imaging of Chiral Amino Acids in Agar Gel through Circularly Polarized Luminescence of EuIII Complex.
Koike H1, Nozaki K1, Iwamura M1.
2020 Jan 2
L-Hisidine is an essential amino acid for infants. L-Hisidine is an inhibitor of mitochondrial glutamine transport.