Comparison of oligosaccharide labeling employing reductive amination and hydrazone formation chemistries

0522452 - ÚIACH 2021 RIV DE eng J - Journal Article
Křenková, Jana - Duša, Filip - Čmelík, Richard
Comparison of oligosaccharide labeling employing reductive amination and hydrazone formation chemistries.
Electrophoresis. Roč. 41, č. 9 (2020), s. 684-690. ISSN 0173-0835. E-ISSN 1522-2683
R&D Projects: GA ČR(CZ) GA18-00062S
Grant - others:AV ČR(CZ) MTA-19-06
Program: Bilaterální spolupráce
Institutional support: RVO:68081715
Keywords : hydrazone formation * labeling * oligosaccharides * reductive amination
OECD category: Analytical chemistry
Impact factor: 3.535, year: 2020
Method of publishing: Limited access

In this work, we compare labeling by two negatively charged fluorescent labels, 8-aminopyrene-1,3,6-trisulfonic acid (APTS) and 8-(2-hydrazino-2-oxoethoxy)pyrene-1,3,6-
trisulfonic acid (Cascade Blue hydrazide [CBH]). Effectiveness of the labeling chemistries were investigated by 4-hydroxybenzaldehyde and maltoheptaose followed by LC/UV-MS
and CE/LIF analysis, respectively. The reaction yield of APTS labeling was determined to be only ∼10%. This is due to reduction of almost 90% of the analyte by sodium cyanoborohydride
to alcohol, which cannot be further labeled via reductive amination. However, the CBH labeling provides ∼90% reaction yield based on the LC/UV-MS measurements. The
significantly higher labeling yield was also confirmed by CE/LIF measurements. Finally, the more effective hydrazone formation technique of CBH was characterized and applied
for N-linked glycan analysis by CE/LIF.
Permanent Link: http://hdl.handle.net/11104/0306941