Investigations in the field of the mass spectrometry of amino acid derivatives Communication 3. Mass spectra of phenylthiohydantoins of aliphatic amino acids containing a functional group in the alkyl chain

1966 ◽  
Vol 15 (10) ◽  
pp. 1656-1661
Author(s):  
A. M. Zyakun ◽  
V. A. Puchkov ◽  
V. M. Stepanov ◽  
N. S. Vul'fson
Keyword(s):  
Mass Spectrometry ◽  
Amino Acids ◽  
Amino Acid ◽  
Mass Spectra ◽  
Functional Group ◽  
Alkyl Chain ◽  
Amino Acid Derivatives

Massenspektrometrische Identifizierung der Phenylthiohydantoin-Derivate von Aminosäuren / Identification of Amino Acid Phenylthiohydantoins by Mass Spectrometry

1970 ◽  
Vol 25 (7) ◽  
pp. 681-689 ◽  
Author(s):  
H. Hagenmaier ◽  
W. Ebbighausen ◽  
G. Nicholson ◽  
W. Vötsch
Keyword(s):  
Mass Spectrometry ◽  
Amino Acids ◽  
Gas Chromatography ◽  
Amino Acid ◽  
Mass Spectra ◽  
Gas Chromatography Mass Spectrometry ◽  
Chromatography Mass Spectrometry ◽  
Unequivocal Identification

The unequivocal identification of phenylthiohydantoins of the 20 amino acids usually occurring in proteins is possible by mass spectrometry and by combined gas chromatography-mass spectrometry. The method is sensitive enough to be applied to the identification of phenylthiohydantoins obtained from automated Edman degradations of polypeptides. Mass spectra of 21 amino acid phenylthiohydantoins are presented and interpreted.

Stereoselective Reaction Mass Spectrometry with Cyclic α-Amino Acids

1991 ◽  
Vol 46 (3) ◽  
pp. 320-325 ◽  
Author(s):  
Jürgen Martens ◽  
Stefan Lübben ◽  
Walter Schwarting
Keyword(s):  
Mass Spectrometry ◽  
Amino Acids ◽  
Amino Acid ◽  
Absolute Configuration ◽  
Mass Spectra ◽  
Reaction Mass ◽  
Chiral Selector ◽  
Enantiomerically Pure ◽  
Stereoselective Reaction ◽  
The Absolute

Stereoselective reaction mass spectrometry in the chemical ionization (isobutane) mode has been used to detect the absolute configuration of enantiomerically pure cyclic α-amino acids. Thus, an enantiomerically pure cyclic α-amino acid was allowed to react on a micromole level with both enantiomers of a chiral selector and the mass spectra were detected. The relative abundances of characteristic ions formed by the diastereoselective reaction between the α-amino acid and the chiral selector of the same configuration were much higher than those ions formed by the α-amino acid and the chiral selector of a different configuration. The absolute configuration of the α-amino acid may be predicted by careful examination of the two stereoselective reaction mass spectra of the α-amino acid measured with both, the chiral (R)-and (S)-selector respectively. Various (R)- and (S)-carboxylic acids and (R)- and (S)-α-phenylethyl amine have been used as chiral selectors.

scholarly journals Mass spectrometry imaging of L-[ring-13C6]-labeled phenylalanine and tyrosine kinetics in non-small cell lung carcinoma

2021 ◽  
Vol 9 (1) ◽  
Author(s):  
Jianhua Cao ◽  
Benjamin Balluff ◽  
Martijn Arts ◽  
Ludwig J. Dubois ◽  
Luc J. C. van Loon ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Amino Acids ◽  
Amino Acid ◽  
Mass Spectrometry Imaging ◽  
Tumor Tissue ◽  
Small Cell Lung Carcinoma ◽  
Small Cell ◽  
Small Cell Lung ◽  
Tracer Injection ◽  
Cell Lung Carcinoma

Abstract Background Metabolic reprogramming is a common phenomenon in tumorigenesis and tumor progression. Amino acids are important mediators in cancer metabolism, and their kinetics in tumor tissue are far from being understood completely. Mass spectrometry imaging is capable to spatiotemporally trace important endogenous metabolites in biological tissue specimens. In this research, we studied L-[ring-13C6]-labeled phenylalanine and tyrosine kinetics in a human non-small cell lung carcinoma (NSCLC) xenografted mouse model using matrix-assisted laser desorption/ionization Fourier-transform ion cyclotron resonance mass spectrometry imaging (MALDI-FTICR-MSI). Methods We investigated the L-[ring-13C6]-Phenylalanine (13C6-Phe) and L-[ring-13C6]-Tyrosine (13C6-Tyr) kinetics at 10 min (n = 4), 30 min (n = 3), and 60 min (n = 4) after tracer injection and sham-treated group (n = 3) at 10 min in mouse-xenograft lung tumor tissues by MALDI-FTICR-MSI. Results The dynamic changes in the spatial distributions of 19 out of 20 standard amino acids are observed in the tumor tissue. The highest abundance of 13C6-Phe was detected in tumor tissue at 10 min after tracer injection and decreased progressively over time. The overall enrichment of 13C6-Tyr showed a delayed temporal trend compared to 13C6-Phe in tumor caused by the Phe-to-Tyr conversion process. Specifically, 13C6-Phe and 13C6-Tyr showed higher abundances in viable tumor regions compared to non-viable regions. Conclusions We demonstrated the spatiotemporal intra-tumoral distribution of the essential aromatic amino acid 13C6-Phe and its de-novo synthesized metabolite 13C6-Tyr by MALDI-FTICR-MSI. Our results explore for the first time local phenylalanine metabolism in the context of cancer tissue morphology. This opens a new way to understand amino acid metabolism within the tumor and its microenvironment.

scholarly journals Determination of free amino acids in plants by liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS)

2015 ◽  
Vol 7 (18) ◽  
pp. 7574-7581 ◽  
Author(s):  
Magdalena M. Dziągwa-Becker ◽  
Jose M. Marin Ramos ◽  
Jakub K. Topolski ◽  
Wiesław A. Oleszek
Keyword(s):  
Mass Spectrometry ◽  
Amino Acids ◽  
Liquid Chromatography ◽  
Amino Acid ◽  
Tandem Mass Spectrometry ◽  
Free Amino ◽  
Tandem Mass ◽  
Amino Acid Determination ◽  
Acid Determination

Free amino acid determination in plants by LC-MS/MS.

scholarly journals Detection of Structural and Conformational Changes in ALS-Causing Mutant Profilin1 With Hydrogen/Deuterium Exchange Mass Spectrometry and Bioinformatics Techniques

2021 ◽  
Author(s):  
Ahmad Shahir Sadr ◽  
zahra abdollahpour ◽  
Atousa Aliahmadi ◽  
Changiz Eslahchi ◽  
Mina Nekouei ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Amino Acids ◽  
Amino Acid ◽  
Conformational Changes ◽  
Docking Simulation ◽  
Hydrogen Deuterium Exchange ◽  
Maldi Tof Ms ◽  
Maldi Tof ◽  
Hydrogen Deuterium ◽  
Tof Ms

Abstract The hydrogen/deuterium exchange (HDX) is a reliable method to survey the dynamic behavior of proteins and epitope mapping. Matrix-Assisted Laser Desorption Ionization-Time of Flight Mass Spectrometry (MALDI-TOF MS) is a quantifying tool to assay for HDX in the protein of interest. We combined HDX-MALDI-TOF MS and molecular docking/MD simulation to identify accessible amino acids and analyze their contribution in the structural changes of profilin1 (PFN1). The molecular docking/MD simulations are computational tools for enabling the analysis of the type of amino acids that may be involved via HDX identified under the lowest binding energy condition. Glycine to Valine amino acid (G117V) substitution mutation is linked to amyotrophic lateral sclerosis (ALS). This mutation is found to be in the actin-binding site of PFN1 and prevents the dimerization/polymerization of actin and invokes a pathologic toxicity that leads to ALS. In this study, we sought to understand the PFN1 protein dynamic behavior using purified wild type and mutant PFN1 proteins. The data obtained from HDX-MALDI-TOF MS for PFN1WT and PFN1G117V at various time intervals, from seconds to hours, revealed multiple peaks corresponding to molecular weights from monomers to multimers. PFN1/Benzaldehyde complexes identified 20 accessible amino acids to HDX that participate in the docking simulation in the surface of WT and mutant PFN1. Consistent results from HDX-MALDI-TOF MS and docking simulation predict candidate amino acid(s) involved in the dimerization/polymerization of PFNG117V. This information may shed critical light on the structural and conformational changes with details of amino acid epitopes for mutant PFN1s’ dimerization, oligomerization, and aggregation.

scholarly journals Enantioselective synthesis of α-alkenyl α-amino acids via N–H insertion reactions

2016 ◽  
Vol 7 (2) ◽  
pp. 1104-1108 ◽  
Author(s):  
Jun-Xia Guo ◽  
Ting Zhou ◽  
Bin Xu ◽  
Shou-Fei Zhu ◽  
Qi-Lin Zhou
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Enantioselective Synthesis ◽  
Insertion Reaction ◽  
Amino Acid Derivatives ◽  
Insertion Reactions ◽  
Phosphoric Acids

A new highly enantioselective route to α-alkenyl α-amino acid derivatives using a N–H insertion reaction of vinyldiazoacetates and tert-butyl carbamate cooperatively catalyzed by achiral dirhodium(ii) carboxylates and chiral spiro phosphoric acids was developed.

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