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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Autor principal: Erra Balsells, Rosa
Publicado: 2013
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Acceso en línea: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
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spelling 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
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