Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis
Successful application of matrix-assisted laser desorption/ionization (MALDI) MS started with the introduction of efficient matrices such as cinnamic acid derivatives (i.e. 3,5-dimethoxy-4-hydroxycinnamic acid, SA; α-cyano-4-hydroxycinnamic acid). Since the empirical founding of these matrices, othe...
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paper:paper_10765174_v48_n11_p1160_Salum2023-06-08T16:05:24Z Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis Erra Balsells, Rosa E-coumaric acid E-ferulic acid E-sinapinic acid neutral carbohydrates sulfated carbohydrates Z-coumaric acid Z-ferulic acid Z-sinapinic acid 3 ,5-dihydroxybenzoic acid Cinnamic acid derivatives Crystalline matrices Cyano-4-hydroxycinnamic acids Density functional theory studies Matrix assisted laser desorption/ionization Morphological properties Photochemical stability Chemical bonds Geometry Isomers Stereochemistry Stereoselectivity Carbohydrates anion cinnamic acid ferulic acid para coumaric acid sinapic acid carbohydrate cinnamic acid cinnamic acid derivative coumaric acid sinapic acid amino acid synthesis article carbohydrate analysis carbon nuclear magnetic resonance chemical structure controlled study dissociation high performance liquid chromatography isomer isomerization limit of detection matrix assisted laser desorption ionization time of flight mass spectrometry molecular interaction photochemistry priority journal proton nuclear magnetic resonance solid state stereochemistry ultraviolet spectroscopy chemistry mass spectrometry procedures stereoisomerism Carbohydrates Cinnamates Coumaric Acids Models, Molecular Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Stereoisomerism Successful application of matrix-assisted laser desorption/ionization (MALDI) MS started with the introduction of efficient matrices such as cinnamic acid derivatives (i.e. 3,5-dimethoxy-4-hydroxycinnamic acid, SA; α-cyano-4-hydroxycinnamic acid). Since the empirical founding of these matrices, other commercial available cinnamic acids with different nature and location of substituents at benzene ring were attempted. Rational design and synthesis of new cinnamic acids have been recently described too. Because the presence of a rigid double bond in its molecule structure, cinnamic acids can exist as two different geometric isomers, the E-form and Z-form. Commercial available cinnamic acids currently used as matrices are the geometric isomers trans or E (E-cinnamic and trans-cinnamic acids). As a new rational design of MALDI matrices, Z-cinnamic acids were synthesized, and their properties as matrices were studied. Their performance was compared with that of the corresponding E-isomer and classical crystalline matrices (3,5-dihydroxybenzoic acid; norharmane) in the analysis of neutral/sulfated carbohydrates. Herein, we demonstrate the outstanding performance for Z-SA. Sulfated oligosaccharides were detected in negative ion mode, and the dissociation of sulfate groups was almost suppressed. Additionally, to better understand the quite different performance of each geometric isomer as matrix, the physical and morphological properties as well as the photochemical stability in solid state were studied. The influence of the E/Z photoisomerization of the matrix during MALDI was evaluated. Finally, molecular modeling (density functional theory study) of the optimized geometry and stereochemistry of E-cinnamic and Z-cinnamic acids revealed some factors governing the analyte-matrix interaction. Copyright © 2013 John Wiley & Sons, Ltd. Fil:Erra-Balsells, R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 2013 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10765174_v48_n11_p1160_Salum http://hdl.handle.net/20.500.12110/paper_10765174_v48_n11_p1160_Salum |
institution |
Universidad de Buenos Aires |
institution_str |
I-28 |
repository_str |
R-134 |
collection |
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
topic |
E-coumaric acid E-ferulic acid E-sinapinic acid neutral carbohydrates sulfated carbohydrates Z-coumaric acid Z-ferulic acid Z-sinapinic acid 3 ,5-dihydroxybenzoic acid Cinnamic acid derivatives Crystalline matrices Cyano-4-hydroxycinnamic acids Density functional theory studies Matrix assisted laser desorption/ionization Morphological properties Photochemical stability Chemical bonds Geometry Isomers Stereochemistry Stereoselectivity Carbohydrates anion cinnamic acid ferulic acid para coumaric acid sinapic acid carbohydrate cinnamic acid cinnamic acid derivative coumaric acid sinapic acid amino acid synthesis article carbohydrate analysis carbon nuclear magnetic resonance chemical structure controlled study dissociation high performance liquid chromatography isomer isomerization limit of detection matrix assisted laser desorption ionization time of flight mass spectrometry molecular interaction photochemistry priority journal proton nuclear magnetic resonance solid state stereochemistry ultraviolet spectroscopy chemistry mass spectrometry procedures stereoisomerism Carbohydrates Cinnamates Coumaric Acids Models, Molecular Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Stereoisomerism |
spellingShingle |
E-coumaric acid E-ferulic acid E-sinapinic acid neutral carbohydrates sulfated carbohydrates Z-coumaric acid Z-ferulic acid Z-sinapinic acid 3 ,5-dihydroxybenzoic acid Cinnamic acid derivatives Crystalline matrices Cyano-4-hydroxycinnamic acids Density functional theory studies Matrix assisted laser desorption/ionization Morphological properties Photochemical stability Chemical bonds Geometry Isomers Stereochemistry Stereoselectivity Carbohydrates anion cinnamic acid ferulic acid para coumaric acid sinapic acid carbohydrate cinnamic acid cinnamic acid derivative coumaric acid sinapic acid amino acid synthesis article carbohydrate analysis carbon nuclear magnetic resonance chemical structure controlled study dissociation high performance liquid chromatography isomer isomerization limit of detection matrix assisted laser desorption ionization time of flight mass spectrometry molecular interaction photochemistry priority journal proton nuclear magnetic resonance solid state stereochemistry ultraviolet spectroscopy chemistry mass spectrometry procedures stereoisomerism Carbohydrates Cinnamates Coumaric Acids Models, Molecular Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Stereoisomerism Erra Balsells, Rosa Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis |
topic_facet |
E-coumaric acid E-ferulic acid E-sinapinic acid neutral carbohydrates sulfated carbohydrates Z-coumaric acid Z-ferulic acid Z-sinapinic acid 3 ,5-dihydroxybenzoic acid Cinnamic acid derivatives Crystalline matrices Cyano-4-hydroxycinnamic acids Density functional theory studies Matrix assisted laser desorption/ionization Morphological properties Photochemical stability Chemical bonds Geometry Isomers Stereochemistry Stereoselectivity Carbohydrates anion cinnamic acid ferulic acid para coumaric acid sinapic acid carbohydrate cinnamic acid cinnamic acid derivative coumaric acid sinapic acid amino acid synthesis article carbohydrate analysis carbon nuclear magnetic resonance chemical structure controlled study dissociation high performance liquid chromatography isomer isomerization limit of detection matrix assisted laser desorption ionization time of flight mass spectrometry molecular interaction photochemistry priority journal proton nuclear magnetic resonance solid state stereochemistry ultraviolet spectroscopy chemistry mass spectrometry procedures stereoisomerism Carbohydrates Cinnamates Coumaric Acids Models, Molecular Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization Stereoisomerism |
description |
Successful application of matrix-assisted laser desorption/ionization (MALDI) MS started with the introduction of efficient matrices such as cinnamic acid derivatives (i.e. 3,5-dimethoxy-4-hydroxycinnamic acid, SA; α-cyano-4-hydroxycinnamic acid). Since the empirical founding of these matrices, other commercial available cinnamic acids with different nature and location of substituents at benzene ring were attempted. Rational design and synthesis of new cinnamic acids have been recently described too. Because the presence of a rigid double bond in its molecule structure, cinnamic acids can exist as two different geometric isomers, the E-form and Z-form. Commercial available cinnamic acids currently used as matrices are the geometric isomers trans or E (E-cinnamic and trans-cinnamic acids). As a new rational design of MALDI matrices, Z-cinnamic acids were synthesized, and their properties as matrices were studied. Their performance was compared with that of the corresponding E-isomer and classical crystalline matrices (3,5-dihydroxybenzoic acid; norharmane) in the analysis of neutral/sulfated carbohydrates. Herein, we demonstrate the outstanding performance for Z-SA. Sulfated oligosaccharides were detected in negative ion mode, and the dissociation of sulfate groups was almost suppressed. Additionally, to better understand the quite different performance of each geometric isomer as matrix, the physical and morphological properties as well as the photochemical stability in solid state were studied. The influence of the E/Z photoisomerization of the matrix during MALDI was evaluated. Finally, molecular modeling (density functional theory study) of the optimized geometry and stereochemistry of E-cinnamic and Z-cinnamic acids revealed some factors governing the analyte-matrix interaction. Copyright © 2013 John Wiley & Sons, Ltd. |
author |
Erra Balsells, Rosa |
author_facet |
Erra Balsells, Rosa |
author_sort |
Erra Balsells, Rosa |
title |
Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis |
title_short |
Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis |
title_full |
Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis |
title_fullStr |
Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis |
title_full_unstemmed |
Z-sinapinic acid: The change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate MALDI-MS analysis |
title_sort |
z-sinapinic acid: the change of the stereochemistry of cinnamic acids as rational synthesis of a new matrix for carbohydrate maldi-ms analysis |
publishDate |
2013 |
url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10765174_v48_n11_p1160_Salum http://hdl.handle.net/20.500.12110/paper_10765174_v48_n11_p1160_Salum |
work_keys_str_mv |
AT errabalsellsrosa zsinapinicacidthechangeofthestereochemistryofcinnamicacidsasrationalsynthesisofanewmatrixforcarbohydratemaldimsanalysis |
_version_ |
1768545104975364096 |