Differentiation of Sialyl Linkages Using a Combination of Alkyl
Esterification and Phenylhydrazine Derivatization: Application
for N-Glycan Profiling in the Sera of Patients with Lung Cancer

J 2022

Differentiation of Sialyl Linkages Using a Combination of Alkyl Esterification and Phenylhydrazine Derivatization: Application for N-Glycan Profiling in the Sera of Patients with Lung Cancer

JEŽKOVÁ, Petra, Jana SKŘIČKOVÁ, Gejza WIMMER, Jana ZELINKOVÁ, Zbyněk ZDRÁHAL et. al.

Základní údaje

Originální název

Differentiation of Sialyl Linkages Using a Combination of Alkyl Esterification and Phenylhydrazine Derivatization: Application for N-Glycan Profiling in the Sera of Patients with Lung Cancer

Autoři

JEŽKOVÁ, Petra (203 Česká republika, domácí), Jana SKŘIČKOVÁ (203 Česká republika), Gejza WIMMER (703 Slovensko), Jana ZELINKOVÁ (203 Česká republika, domácí), Zbyněk ZDRÁHAL (203 Česká republika, domácí) a Erika LATTOVÁ (703 Slovensko, garant, domácí)

Vydání

ANALYTICAL CHEMISTRY, UNITED STATES, AMER CHEMICAL SOC, 2022, 0003-2700

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10406 Analytical chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

fulltext

Impakt faktor

Impact factor: 7.400

Kód RIV

RIV/00216224:14740/22:00125948

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1021/acs.analchem.2c00105

UT WoS

000798539200014

Klíčová slova anglicky

Mass-spectrometric analysis; Structural-characterization; Acid derivatization; Glycosylation; Adenocarcinoma; Oligosaccharides; Stabilization; Glycoproteins

Štítky

CF PROT, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 2. 11. 2024 21:03, Ing. Martina Blahová

Anotace

V originále

Alterations in oligosaccharides and types of sialic acid (SA) attachments have been associated with different pathological states. Matrix-assisted laser desorption mass spectrometry (MS) is commonly used for glycosylation studies. However, native sialylated glycans are suppressed or not detected during MS experiments. Consequently, different approaches have been employed to neutralize the negative charge of the carboxyl group. In this study, we present the advantage of phenylhydrazine (PHN) labeling for the detection and efficient discrimination of SA linkages when this derivatization follows alkyl esterification. As expected, PHN-labeled sialylated oligosaccharides with the 2,6-linkage type can be easily recognized according to the additional shift in mass corresponding to the presence of a methyl or ethyl group. Surprisingly, oligosaccharides with the 2,3-linked SA residue instead of a lactone were detected carrying the second PHN unit. This was beneficial as no further processing after esterification was needed to stabilize the lactone form. Moreover, during tandem mass experiments, all modified glycans produced favorable fragmentation patterns with a coherent recognition of SA linkages. Although both types of esterification, herein called the EST-PHN approach, provided comparable results, methylation exhibited marginally higher linkage specificity than ethyl esterification. The simplicity and effectiveness of the methodology are demonstrated on the model compound, sialyllactose, and its applicability for biological studies is presented on N-glycan profiling in the sera of lung cancer patients.

Návaznosti

EF18_046/0015974, projekt VaV

Název: Modernizace České infrastruktury pro integrativní strukturní biologii

90127, velká výzkumná infrastruktura

Název: CIISB II

Citovat

JEŽKOVÁ, Petra, Jana SKŘIČKOVÁ, Gejza WIMMER, Jana ZELINKOVÁ, Zbyněk ZDRÁHAL a Erika LATTOVÁ. Differentiation of Sialyl Linkages Using a Combination of Alkyl Esterification and Phenylhydrazine Derivatization: Application for N-Glycan Profiling in the Sera of Patients with Lung Cancer. ANALYTICAL CHEMISTRY. UNITED STATES: AMER CHEMICAL SOC, 2022, roč. 94, č. 18, s. 6736-6744. ISSN 0003-2700. Dostupné z: https://dx.doi.org/10.1021/acs.analchem.2c00105.

@article{1858721,
   author = {Ježková, Petra and Skřičková, Jana and Wimmer, Gejza and Zelinková, Jana and Zdráhal, Zbyněk and Lattová, Erika},
   article_location = {UNITED STATES},
   article_number = {18},
   doi = {http://dx.doi.org/10.1021/acs.analchem.2c00105},
   keywords = {Mass-spectrometric analysis; Structural-characterization; Acid derivatization; Glycosylation; Adenocarcinoma; Oligosaccharides; Stabilization; Glycoproteins},
   language = {eng},
   issn = {0003-2700},
   journal = {ANALYTICAL CHEMISTRY},
   title = {Differentiation of Sialyl Linkages Using a Combination of Alkyl Esterification and Phenylhydrazine Derivatization: Application for N-Glycan Profiling in the Sera of Patients with Lung Cancer},
   url = {https://pubs.acs.org/doi/10.1021/acs.analchem.2c00105},
   volume = {94},
   year = {2022}
}

TY  - JOUR
ID  - 1858721
AU  - Ježková, Petra - Skřičková, Jana - Wimmer, Gejza - Zelinková, Jana - Zdráhal, Zbyněk - Lattová, Erika
PY  - 2022
TI  - Differentiation of Sialyl Linkages Using a Combination of Alkyl Esterification and Phenylhydrazine Derivatization: Application for N-Glycan Profiling in the Sera of Patients with Lung Cancer
JF  - ANALYTICAL CHEMISTRY
VL  - 94
IS  - 18
SP  - 6736-6744
EP  - 6736-6744
PB  - AMER CHEMICAL SOC
SN  - 00032700
KW  - Mass-spectrometric analysis
KW  - Structural-characterization
KW  - Acid derivatization
KW  - Glycosylation
KW  - Adenocarcinoma
KW  - Oligosaccharides
KW  - Stabilization
KW  - Glycoproteins
UR  - https://pubs.acs.org/doi/10.1021/acs.analchem.2c00105
N2  - Alterations in oligosaccharides and types of sialic acid (SA) attachments have been associated with different pathological states. Matrix-assisted laser desorption mass spectrometry (MS) is commonly used for glycosylation studies. However, native sialylated glycans are suppressed or not detected during MS experiments. Consequently, different approaches have been employed to neutralize the negative charge of the carboxyl group. In this study, we present the advantage of phenylhydrazine (PHN) labeling for the detection and efficient discrimination of SA linkages when this derivatization follows alkyl esterification. As expected, PHN-labeled sialylated oligosaccharides with the 2,6-linkage type can be easily recognized according to the additional shift in mass corresponding to the presence of a methyl or ethyl group. Surprisingly, oligosaccharides with the 2,3-linked SA residue instead of a lactone were detected carrying the second PHN unit. This was beneficial as no further processing after esterification was needed to stabilize the lactone form. Moreover, during tandem mass experiments, all modified glycans produced favorable fragmentation patterns with a coherent recognition of SA linkages. Although both types of esterification, herein called the EST-PHN approach, provided comparable results, methylation exhibited marginally higher linkage specificity than ethyl esterification. The simplicity and effectiveness of the methodology are demonstrated on the model compound, sialyllactose, and its applicability for biological studies is presented on N-glycan profiling in the sera of lung cancer patients.
ER  -

JEŽKOVÁ, Petra, Jana SKŘIČKOVÁ, Gejza WIMMER, Jana ZELINKOVÁ, Zbyněk ZDRÁHAL a Erika LATTOVÁ. Differentiation of Sialyl Linkages Using a Combination of Alkyl Esterification and Phenylhydrazine Derivatization: Application for N-Glycan Profiling in the Sera of Patients with Lung Cancer. \textit{ANALYTICAL CHEMISTRY}. UNITED STATES: AMER CHEMICAL SOC, 2022, roč.~94, č.~18, s.~6736-6744. ISSN~0003-2700. Dostupné z: https://dx.doi.org/10.1021/acs.analchem.2c00105.

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