Identification of sialic acid linkage isomers in glycans using coupled InfraRed Multiple Photon Dissociation (IRMPD) spectroscopy and mass spectrometry

2018 ◽  
Vol 434 ◽  
pp. 65-69 ◽  
Author(s):  
Agathe Depraz Depland ◽  
Gina Renois-Predelus ◽  
Baptiste Schindler ◽  
Isabelle Compagnon
Keyword(s):  
Mass Spectrometry ◽  
Sialic Acid ◽  
Irmpd Spectroscopy ◽  
Linkage Isomers ◽  
Infrared Multiple Photon Dissociation ◽  
Sialic Acid Linkage

Chiral differentiation of d- and l-isoleucine using permethylated β-cyclodextrin: infrared multiple photon dissociation spectroscopy, ion-mobility mass spectrometry, and DFT calculations

2018 ◽  
Vol 20 (48) ◽  
pp. 30428-30436 ◽  
Author(s):  
Sung-Sik Lee ◽  
Jae-ung Lee ◽  
Ju Hyeon Oh ◽  
Soojin Park ◽  
Yin Hong ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Dft Calculations ◽  
Ion Mobility ◽  
Ion Mobility Mass Spectrometry ◽  
Irmpd Spectroscopy ◽  
Infrared Multiple Photon Dissociation ◽  
Covalent Complex

d-/l-Isoleucine chirality could be differentiated using IRMPD spectroscopy, ion-mobility mass spectrometry, and DFT calculations for the permethylated β-cyclodextrin non-covalent complex.

Rapid Identification of Terminal Sialic Acid Linkage Isomers by Pseudo-MS3Mass Spectrometry

2015 ◽  
Vol 55 (3-4) ◽  
pp. 412-422 ◽  
Author(s):  
Chein-Hung Chen ◽  
Ya-Ping Lin ◽  
Jung-Lee Lin ◽  
Shiou-Ting Li ◽  
Chien-Tai Ren ◽  
...  
Keyword(s):  
Sialic Acid ◽  
Rapid Identification ◽  
Linkage Isomers ◽  
Terminal Sialic Acid ◽  
Sialic Acid Linkage

scholarly journals The structure and role of lactone intermediates in linkage-specific sialic acid derivatization reactions

2021 ◽  
Author(s):  
Tamas Pongracz ◽  
Aswin Verhoeven ◽  
Manfred Wuhrer ◽  
Noortje de Haan
Keyword(s):  
Mass Spectrometry ◽  
Sialic Acid ◽  
Method Development ◽  
Sialic Acids ◽  
Resonance Spectroscopy ◽  
Reaction Conditions ◽  
Linkage Isomers ◽  
Amide Derivatives ◽  
Complex Glycan

AbstractSialic acids occur ubiquitously throughout vertebrate glycomes and often endcap glycans in either α2,3- or α2,6-linkage with diverse biological roles. Linkage-specific sialic acid characterization is increasingly performed by mass spectrometry, aided by differential sialic acid derivatization to discriminate between linkage isomers. Typically, during the first step of such derivatization reactions, in the presence of a carboxyl group activator and a catalyst, α2,3-linked sialic acids condense with the subterminal monosaccharides to form lactones, while α2,6-linked sialic acids form amide or ester derivatives. In a second step, the lactones are converted into amide derivatives. Notably, the structure and role of the lactone intermediates in the reported reactions remained ambiguous, leaving it unclear to which extent the amidation of α2,3-linked sialic acids depended on direct aminolysis of the lactone, rather than lactone hydrolysis and subsequent amidation. In this report, we used mass spectrometry to unravel the role of the lactone intermediate in the amidation of α2,3-linked sialic acids by applying controlled reaction conditions on simple and complex glycan standards. The results unambiguously show that in common sialic acid derivatization protocols prior lactone formation is a prerequisite for the efficient, linkage-specific amidation of α2,3-linked sialic acids, which proceeds predominantly via direct aminolysis. Furthermore, nuclear magnetic resonance spectroscopy confirmed that exclusively the C2 lactone intermediate is formed on a sialyllactose standard. These insights allow a more rationalized method development for linkage-specific sialic derivatization in the future.

Differentiation of Sialyl Linkage Isomers by One-Pot Sialic Acid Derivatization for Mass Spectrometry-Based Glycan Profiling

2017 ◽  
Vol 89 (4) ◽  
pp. 2353-2360 ◽  
Author(s):  
Takashi Nishikaze ◽  
Hiroki Tsumoto ◽  
Sadanori Sekiya ◽  
Shinichi Iwamoto ◽  
Yuri Miura ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Sialic Acid ◽  
One Pot ◽  
Linkage Isomers ◽  
Glycan Profiling

scholarly journals Glycan-protein cross-linking mass spectrometry reveals sialic acid-mediated protein networks on cell surfaces

2021 ◽  
Author(s):  
Yixuan Xie ◽  
Siyu Chen ◽  
Qiongyu Li ◽  
Ying Sheng ◽  
Michael R Alvarez ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Sialic Acid ◽  
Membrane Proteins ◽  
Cell Membranes ◽  
Sialic Acids ◽  
Cross Linking ◽  
Protein Networks ◽  
Cell Surfaces ◽  
Protein Cross Linking

A cross-linking method is developed to elucidate the glycan-mediated interactions between membrane proteins through sialic acids. The method provides previously unknown extensive glycomic interactions on cell membranes. The vast majority...

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