Publications related to C(1 -> 4)-linked disaccharides through carbonylative Stille cross-coupling

A New Strategy Coupling Ion-Mobility-Selective CID and Cryogenic IR Spectroscopy to Identify Glycan Anomers

Thomas Rizzo, Ahmed Ben Faleh, Robert Paul Pellegrinelli, Stephan Warnke, Priyanka Bansal, Eduardo Carrascosa Casado, Lei Yue

Determining the primary structure of glycans remains challenging due to their isomeric complexity. While high-resolution ion mobility spectrometry (IMS) has recently allowed distinguishing between many glycan isomers, the arrival-time distributions (ATDs) ...

2022

Identification of Mobility-Resolved N-Glycan Isomers

Thomas Rizzo, Ahmed Ben Faleh, Robert Paul Pellegrinelli, Stephan Warnke, Priyanka Bansal

Glycan analysis has evolved considerably during the last decade. The advent of high-resolution ion-mobility spectrometry has enabled the separation of isomers with only the slightest of structural differences. However, the ability to separate such species ...

AMER CHEMICAL SOC2022

Combining multi-stage ion mobility spectrometry with cryogenic infrared spectroscopy for glycan analysis

Priyanka Bansal

Structural analysis of biomolecules is essential to understanding biological processes. Among the various classes of biomolecules, glycans have gained significant attention recently due to their ubiquitous roles in biological systems. However, study of gly ...

EPFL2022

Identifying Mixtures of Isomeric Human Milk Oligosaccharides by the Decomposition of IR Spectral Fingerprints

Thomas Rizzo, Ahmed Ben Faleh, Stephan Warnke, Ali H Abikhodr, Vasyl Yatsyna

The analysis of glycans presents a significant challenge that arises from their isomeric heterogeneity. While high-resolution ion mobility spectrometry (IMS) has shown the ability to resolve subtly different glycan isomers, their unambiguous assignment rem ...

2021

Combining cryognic ion spectroscopy with ion mobility for the study of glycan fragmentation

Robert Paul Pellegrinelli

The importance of glycans in biological processes are matched by their structural complexity. Coating the surface of most living cells, glycans play key roles in many biological processes, and the role they play is closely related to their structures. Stru ...

EPFL2021

Equilibrium and non-equilibrium furanose selection in the ribose isomerisation network

Paolo De Los Rios, Francesco Piazza, Shiling Liang, Daniel Maria Busiello

The exclusive presence of beta -D-ribofuranose in nucleic acids is still a conundrum in prebiotic chemistry, given that pyranose species are substantially more stable at equilibrium. However, a precise characterisation of the relative furanose/pyranose fra ...

Nature Research2021

Cryogenic Ion Spectroscopy for Identification of Monosaccharide Anomers

Thomas Rizzo, Valeriu Scutelnic

We combine conformer-selective, cryogenic infrared spectroscopy, quantum mechanical computations, and 18O substitution at the reducing end to determine the structural preferences of protonated glucosamine in the gas phase. Cryogenic infrared-infrared (IR-I ...

2019

Production, characterization and upgrading of biomass-derived acetal-stabilized carbohydrates

Ydna Marie Questell-Santiago

Biomass is an attractive source of renewable carbon-based fuels and chemicals. Multiple research efforts are centered around integrated biorefineries, where all fractions of biomass are converted to fuels or chemical products. These efforts are focused aro ...

EPFL2019

Interplay of H-Bonds with Aromatics in Isolated Complexes Identifies Isomeric Carbohydrates

Oleg Boyarkine, Vladimir Kopysov, Aleksandr Pereverzev, Ruslan Yamaletdinov

The tremendous isomeric diversity of carbohydrates enables a wide range of their biological functions but makes the identification and study of these molecules difficult. We investigated the ability of intermolecular interactions to communicate structural ...

Wiley-VCH Verlag GmbH2019

Generation of Heteroatom Stereocenters by Enantioselective C-H Functionalization

Nicolai Cramer, Johannes Diesel

C-H functionalization has been established as an efficient way to generate molecular complexity. The formation of stereogenic carbon atoms by asymmetric C-H functionalization has seen tremendous progress over the past decade. More recently, the direct cata ...

2019

Cryogenic Vibrational Spectroscopy Provides Unique Fingerprints for Glycan Identification

Thomas Rizzo, Michael Zachary Kamrath, Chiara Masellis, Neelam Khanal

The structural characterization of glycans by mass spectrometry is particularly challenging. This is because of the high degree of isomerism in which glycans of the same mass can differ in their stereochemistry, attachment points, and degree of branching. ...

2017

Redefining the metabolic landscape through TGF-beta/Activin signaling in Drosophila melanogaster

Wen Bin Chng

Multicellular organisms assess their nutritional state and adapt their metabolic landscape to match their energy demands. In this thesis, we address a longstanding conundrum of how an organism coordinates digestive enzyme expression in response to its nutr ...

EPFL2015

Toward Quantitative Measurements of Enzyme Kinetics by Dissolution Dynamic Nuclear Polarization

Geoffrey Bodenhausen, Sami Jannin, Aurélien Bornet, Jonas Milani, Daniel Abergel

Dissolution dynamic nuclear polarization (D-DNP) experiments enabled us to study the kinetics of the enzymatic phosphorylation reaction of glucose to form glucose-6-phosphate (G6P) by hexokinase (HK), with or without the presence of an excess of G6P, which ...

2014

Enhanced Conversion of Carbohydrates to the Platform Chemical 5-Hydroxymethylfurfural Using Designer Ionic Liquids

Gabor Laurenczy, Rosario Scopelliti, Paul Joseph Dyson, Zhaofu Fei, Ning Yan, Sviatlana Siankevich

5-Hydroxymethylfurfural (HMF) is a key platform chemical that may be obtained from various cellulosic (biomass) derivatives. Previously, it has been shown that ionic liquids (ILs) facilitate the catalytic conversion of glucose into HMF. Herein, we demonstr ...

Wiley-V C H Verlag Gmbh2014

Synthesis of C-linked Disaccharides and Analogues as Biomimetics of the TF Epitope

Maria Kolympadi

Glycoproteins and glycolipids are major components of the outer surface of mammalian cells. Their carbohydrate moieties, which are directed into the outer environment, serve as ligands for receptor proteins, such as lectins, pathogen proteins and antibodie ...

EPFL2011

Synthesis and glycosidase inhibitory activity of 1-amino-3,6-anhydro-1-deoxy-D-sorbitol derivatives

Pierre Vogel, Claudia Bello

3,6-Anhydro-1-(aryl or alkylamino)-1-deoxy-D-sorbitol derivatives have been prepared in four steps from isosorbide, a by-product from the starch industry. The inhibitory activities of these new compounds have been evaluated towards 13 glycosidases. A first ...

2010

Recent Synthetic Approaches Toward Non-anomeric Spiroketals in Natural Products

Pierre Vogel, Sandrine Gerber, Sylvain Favre

Many natural products of biological interest contain [6,5]- and [6,6]-spiroketal moieties that can adopt various configurations, benefiting or not from anomeric conformation stabilizing effects. The spiroketal fragments are often important for the biologic ...

2008

Synthesis of monosaccharides and analogues - Part three: Monosaccharides from simple achiral unsaturated compounds

Pierre Vogel, Inmaculada Robina

Nowadays any natural and non-natural monosaccharide can be prepared pure in both enantiomeric forms starting from inexpensive starting materials. Depending on the target, pure chemical procedures relying upon asymmetric catalysis using either metallic or p ...

2007

Implantable glucose sensor : an approach based on a rotating microviscometer combined with a sensitive liquid containing dextran and Concanavalin A

For more than thirty years there has been a high demand for glucose measuring devices to replace the finger pricking methods and to improve the life quality of diabetics. Three approaches are possible, electrochemical, electromagnetic (including optical), ...

EPFL2007

Synthesis of C-glycosides and C-linked disaccharides through carbonylative Stille coupling reactions

Peter Steunenberg

In the first part, we described the synthesis of C-(1'→1) and C-(1'→4) disaccharide precursors, which are readily obtained via the carbonylative Stille coupling of glucal and isolevoglucosenone derivatives. Tin glycals and triflates, derived from isolevogl ...

EPFL2005