Characterization of amino acids and proteinaceous materials using online tetramethylammonium hydroxide (TMAH) thermochemolysis and gas chromatography-mass spectrometry technique

Zang, Xu; Brown, Johnie C.; Heemst, Jasper D.H van; Palumbo, Amanda M.; Hatcher, Patrick G.

doi:10.1016/s0165-2370(01)00151-6

Cited by 46 publications

(38 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…4 An interesting application of this reaction to the analysis of amino acids by GC/MS has been reported. 32,33 This on-line thermochemolysis technique using TMAH enables conversion of amino acids to their N-and O-methyl derivatives in the pyrolysis chamber in 15 s at 300°C. It was shown that all amino, carboxylic and hydroxyl groups, if present, undergo methylation; no rearrangement products such as diketopiperazines were identified among the reaction products:…”

Section: Diazomethane Is Usually Prepared By Reaction Of Nitrosomethymentioning

confidence: 99%

See 1 more Smart Citation

Derivatization in Mass Spectrometry– 3. Alkylation (Arylation)

Halket

Заикин

2004

Eur J Mass Spectrom (Chichester)

View full text Add to dashboard Cite

The review is devoted to alkylation (arylation) as a widely employed derivatization procedure for the protection of OH (carboxylic acids, phosphoric acids, sulfonic acids, alcohols, polyols, phenols, enols), SH (thiols) and NH (amines, amides) groups in order to increase volatility, to improve the chromatographic properties and, if possible, mass spectral properties of derivatives. Chemical aspects of derivatization and various alkylation (arylation) reagents and reaction procedures are described. Specific mass spectral (electron ionization, chemical ionization) features of derivatives helpful in identification, structure elucidation, profiling and quantitative determination of the above-mentioned polar compounds by coupled gas chromatography or high-performance liquid chromatography are discussed. Some common analytical applications of the procedures in organic chemistry, clinical chemistry, environmental chemistry etc. are briefly summarized.

show abstract

Section: Diazomethane Is Usually Prepared By Reaction Of Nitrosomethymentioning

confidence: 99%

“…33 Under thermal conditions, TMAH accomplishes cleavage of the peptide bonds in proteins and peptides and subsequently methylates the released amino acids.…”

Section: Diazomethane Is Usually Prepared By Reaction Of Nitrosomethymentioning

confidence: 99%

Derivatization in Mass Spectrometry– 3. Alkylation (Arylation)

Halket

Заикин

2004

Eur J Mass Spectrom (Chichester)

View full text Add to dashboard Cite

show abstract

“…Since silica surface is acidic because of a number of hydroxyl groups (silanol groups) on the surface, which results in adsorption of polar materials by hydrogen bonds, especially it forms a strong hydrogen bond with basic materials. [19][20][21][22] In previous works, 8,16 the direct methylated products of cysteine, glutamic acid, and glutamine were reported, but these studies used TMAH excess and did not employ silica. Another reason for no direct methylation may have been more favorable other reactions such as cyclization and dissociation processes.…”

Section: Resultsmentioning

confidence: 99%

“…The most efficient reagent was proven to be tetramethylammonium hydroxide (TMAH) which is used as a methylating agent. [8][9][10][11] The application of TMAH thermochemolysis for the study of proteinaceous materials [12][13][14][15] is important because of the significant amounts of proteinaceous materials found in environmentally and geochemically important samples.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Influence of the Structural Characteristics of Amino Acids on Direct Methylation Behaviors by TMAH in Pyrolysis

Choi

2009

Bulletin of the Korean Chemical Society

View full text Add to dashboard Cite

Direct methylation behaviors of 20 amino acids with tetramethylammonium hydroxide (TMAH) were studied under diluted conditions with silica. Amino acid concentration was controlled by dilution with silica (SiO2) and the molar ratios of amino acid/silica were 0.20, 0.50, and 2.0. The molar ratios of amino acid/TMAH (0.51 -4.64) also varied. It was found that arginine, asparagine, aspartic acid, cysteine, glutamic acid, and glutamine did not generate any directly methylated pyrolysis products, whereas alanine, glycine, isoleucine, leucine, methionine, phenylanaline, valine, and proline generated all the directly methylated pyrolysis products. Tri-and tetra methylated products of lysine consisted of two types. Histidine and threonine hardly generated the partly methylated products. Mono-and dimethylated products of serine, tryptophan, and tyrosine were not observed. Relative intensities of the methylated products varied with the amino acid concentration, TMAH concentration, and pyrolysis temperature. Direct methylation behaviors of amino acids were explained by the structural characteristics of amino acids.

show abstract

Py‐GC/MS of Organic Paint Binders

Bonaduce

Andreotti

2009

Organic Mass Spectrometry in Art and Archaeology

View full text Add to dashboard Cite

Characterization of amino acids and proteinaceous materials using online tetramethylammonium hydroxide (TMAH) thermochemolysis and gas chromatography-mass spectrometry technique

Cited by 46 publications

References 22 publications

Derivatization in Mass Spectrometry– 3. Alkylation (Arylation)

Derivatization in Mass Spectrometry– 3. Alkylation (Arylation)

Influence of the Structural Characteristics of Amino Acids on Direct Methylation Behaviors by TMAH in Pyrolysis

Py‐GC/MS of Organic Paint Binders

Contact Info

Product

Resources

About