Synthesis and Application of Novel Fluorescent Labeling Tags for Oligosaccharide and N-Linked Glycan Analysis

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14160%2F23%3A00139107" target="_blank" >RIV/00216224:14160/23:00139107 - isvavai.cz</a>

Výsledek na webu

<a href="http://www.liblice2023.cz/" target="_blank" >http://www.liblice2023.cz/</a>

DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and Application of Novel Fluorescent Labeling Tags for Oligosaccharide and N-Linked Glycan Analysis

Popis výsledku v původním jazyce

Monitoring glycosylation and investigating the influence of glycan structures on their function is an essential area of research, particularly in the diagnosis of disease and the study of mechanisms of pathogenesis.1 Analysis of glycans is still arduous because of their extreme structure complexity and conjugation diversity. But there are also instrumental aspects, such as the sensitivity limits of analyses.2 Therefore, glycan analysis is very often combined with fluorescence detection in addition to MS. In this work, we present the synthesis of novel fluorescent labeling tags for oligosaccharide and N-linked glycan analysis based on the hydrazide derivative of dipyrrometheneboron difluoride (BODIPY) and derivatives of 1,3-diaza-tricyclo[7.3.0.0³,⁷]dodeca-5,7,9,11-tetraene-2,4-dione. Furthermore, we present the application of a newly synthesized hydrazide derivative of BODIPY for oligosaccharide and glycan analysis by high-performance liquid chromatography with fluorescence detection (HPLC/FLD). The labeling method was optimized on maltooligosaccharide standards. The analysis provided the detection limit in the low tens of femtomole, which is at least 30 times more sensitive than the standard approach. In addition, this labeling method was used for N-linked glycan profiling of several glycoproteins by RP-HPLC and HILIC/FLD analysis.

Název v anglickém jazyce

Synthesis and Application of Novel Fluorescent Labeling Tags for Oligosaccharide and N-Linked Glycan Analysis

Popis výsledku anglicky

Monitoring glycosylation and investigating the influence of glycan structures on their function is an essential area of research, particularly in the diagnosis of disease and the study of mechanisms of pathogenesis.1 Analysis of glycans is still arduous because of their extreme structure complexity and conjugation diversity. But there are also instrumental aspects, such as the sensitivity limits of analyses.2 Therefore, glycan analysis is very often combined with fluorescence detection in addition to MS. In this work, we present the synthesis of novel fluorescent labeling tags for oligosaccharide and N-linked glycan analysis based on the hydrazide derivative of dipyrrometheneboron difluoride (BODIPY) and derivatives of 1,3-diaza-tricyclo[7.3.0.0³,⁷]dodeca-5,7,9,11-tetraene-2,4-dione. Furthermore, we present the application of a newly synthesized hydrazide derivative of BODIPY for oligosaccharide and glycan analysis by high-performance liquid chromatography with fluorescence detection (HPLC/FLD). The labeling method was optimized on maltooligosaccharide standards. The analysis provided the detection limit in the low tens of femtomole, which is at least 30 times more sensitive than the standard approach. In addition, this labeling method was used for N-linked glycan profiling of several glycoproteins by RP-HPLC and HILIC/FLD analysis.

Druh

O - Ostatní výsledky

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA22-00236S" target="_blank" >GA22-00236S: Vývoj nových fluorescenčních značek pro elektroforetické analýzy glykoproteinů asociovaných s rakovinou prsu</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů