Synthesis of the 3’-O-sulfated TF antigen with a TEG-N₃ linker for glycodendrimersomes preparation to study lectin binding

• Mark Reihill,
• Hanyue Ma,
• Dennis Bengtsson and
• Stefan Oscarson

Beilstein J. Org. Chem. 2024, 20, 173–180, doi:10.3762/bjoc.20.17

• project with groups from Universities in Munich and Pennsylvania we are investigating carbohydrate–lectin interactions using programmable glycodendrimersomes based on synthetic glycans. We have earlier synthesized 2-[2-(2-azidoethoxy)ethoxy]ethyl (TEG-N3) glycosides of lactose, 3’-Su-lactose and LacdiNAc

Lectins of Mycobacterium tuberculosis – rarely studied proteins

• Katharina Kolbe,
• Sri Kumar Veleti,
• Norbert Reiling and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1

• connected to colonization of the kidney [64][65]. Inhibition of carbohydrate–lectin interactions by antiadhesive drugs is an emerging anti-infective therapeutic approach, particularly in light of increasing rates of bacterial resistance to traditional antibiotics. α-D-Mannosides containing aromatic aglycons

• characterization of lectins. Also in microbe–host cell interactions, specific carbohydrate–lectin interactions are the key to adhesion, microbial colonization as well as to infection. For Mycobacterium tuberculosis it is known that the macrophage-associated lectins Dectin and Mincle, for example, specifically

What contributes to an effective mannose recognition domain?

• Christoph P. Sager,
• Deniz Eriş,
• Martin Smieško,
• Rachel Hevey and
• Beat Ernst

Beilstein J. Org. Chem. 2017, 13, 2584–2595, doi:10.3762/bjoc.13.255

• Christoph P. Sager Deniz Eris Martin Smiesko Rachel Hevey Beat Ernst Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland 10.3762/bjoc.13.255 Abstract In general, carbohydrate–lectin interactions are characterized by high specificity but

• carbohydrate–lectin interactions of the innate immune system but also in bacterial adhesion, a process key for the bacterium’s survival. In an effort to better understand the particular characteristics, which contribute to a successful carbohydrate recognition domain, the mannose-binding sites of six C-type

• described, the various approaches explored by nature to optimize selectivity and affinity of carbohydrate–lectin interactions offer interesting therapeutic perspectives for the development of carbohydrate-based drugs. Keywords: carbohydrate–lectin interactions; desolvation penalty; dielectric constant

Synthesis of D-manno-heptulose via a cascade aldol/hemiketalization reaction

• Yan Chen,
• Xiaoman Wang,
• Junchang Wang and
• You Yang

Beilstein J. Org. Chem. 2017, 13, 795–799, doi:10.3762/bjoc.13.79

• evaluation of carbohydrate–lectin interactions by conjugation with fluorescent quantum dots via click chemistry [13][14]. Besides, differentially protected D-manno-heptulose building blocks could serve as valuable precursors for the synthesis of C-glycosides [15][16]. The known synthesis of D-manno-heptulose

Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar

• Camilla Matassini,
• Stefania Mirabella,
• Andrea Goti,
• Inmaculada Robina,
• Antonio J. Moreno-Vargas and
• Francesca Cardona

Beilstein J. Org. Chem. 2015, 11, 2631–2640, doi:10.3762/bjoc.11.282

• (glycosidases) [1][2]. In quite sharp contrast the multivalent effect, widely investigated in the field of carbohydrate–lectin interactions [3], has remained essentially unexplored concerning glycosidase inhibition up to 2010. Indeed, the first examples of multivalent iminosugars gave disappointing results in

Molecular recognition of surface-immobilized carbohydrates by a synthetic lectin

• Melanie Rauschenberg,
• Eva-Corrina Fritz,
• Christian Schulz,
• Tobias Kaufmann and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 1354–1364, doi:10.3762/bjoc.10.138

• ), respectively. In order to flexibly attach the carbohydrates on the substrate and to ensure unhindered carbohydrate–lectin interactions, oligo(ethylene glycol) spacers were introduced. Oligo(ethylene glycol) chains are flexible, water-soluble and do not interact with lectins [46]. A nucleophilic primary amine

Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks

• Felix Wojcik,
• Sinaida Lel,
• Alexander G. O’Brien,
• Peter H. Seeberger and
• Laura Hartmann

Beilstein J. Org. Chem. 2013, 9, 2395–2403, doi:10.3762/bjoc.9.276

• branched) [18] and biocompatible with a decreased risk of inherent immunogenicity [19]. Recently, we showed that monodisperse, sequence-defined glycooligomers obtained by sequential addition of building blocks on solid support are valuable tools for tuning and understanding carbohydrate–lectin interactions

Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan

• Benjamin Cao,
• Jonathan M. White and
• Spencer J. Williams

Beilstein J. Org. Chem. 2011, 7, 369–377, doi:10.3762/bjoc.7.47

• solubility relative to other common alternatives, and ability to be excited using visible, rather than ultraviolet light [44]. Hindsgaul and coworkers have reported the use of glycoconjugates with NBD dyes to streamline the detection of carbohydrate-lectin interactions and report that the NBD group displayed