Binding of synthetic carbohydrate receptors to enveloped virus glycans: Insights from molecular dynamics simulations

Tapia, Beicer; Yagudayeva, Genrietta; Bravo, M. Fernando; Thakur, Khushabu; Braunschweig, Adam B.; Marianski, Mateusz

doi:10.1016/j.carres.2022.108574

Cited by 2 publications

(3 citation statements)

References 35 publications

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“…[88] In addition, Braunschweig, Marianski, and co-workers explored the binding behavior of flexible synthetic receptors and biologically relevant enveloped virus N-glycans by molecular dynamics simulations. [89]…”

Section: Tetrapodal Receptorsmentioning

confidence: 99%

“…Recently, Braunschweig prepared a new library of flexible SCRs with indole and quinoline heterocyclic groups, including 67 and 68 , and explored regiochemical effects on carbohydrate recognition [88] . In addition, Braunschweig, Marianski, and co‐workers explored the binding behavior of flexible synthetic receptors and biologically relevant enveloped virus N‐glycans by molecular dynamics simulations [89] …”

Section: Flexible Synthetic Receptorsmentioning

confidence: 99%

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Molecular Engineering of Carbohydrate Recognition

2023

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Carbohydrates play a number of structural, functional, and metabolic roles in underpinning natural life processes, acting in states of both health and disease. Given this importance, over millions of years of evolution, living systems have developed an ability to recognize and bind carbohydrates, achieving remarkable recognition affinity and specificity in spite of the often hydrophilic and ubiquitous character of carbohydrate targets. In recent years, bio‐inspired synthetic receptors have been developed to bind carbohydrates, with examples of (pseudo)temple‐shaped receptors, flexible receptors, and dynamic‐covalent/coordinative receptors reported. Certain of these have even demonstrated promising results, for example in binding glucose or exhibiting antiviral and antibiotic function. Accordingly, and in spite of remaining challenges, the development of synthetic receptors for carbohydrate recognition holds great promise to combat some of the most urgent problems facing our world today.

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Section: Tetrapodal Receptorsmentioning

confidence: 99%

Section: Flexible Synthetic Receptorsmentioning

confidence: 99%

Molecular Engineering of Carbohydrate Recognition

2023

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“…Understanding and controlling glycan–lectin interactions at the molecular level is central to the development of diagnostic and therapeutic tools, − engineering new carbohydrate-binding proteins, , and design of materials to scaffold cell growth for regenerative medicine . One challenge in replicating glycan–lectin interactions occurring in vivo is the relatively weak binding (dissociation constant, K D , in the mM range) between individual carbohydrates and lectins .…”

Section: Introductionmentioning

confidence: 99%

Surface-Templated Glycopolymer Nanopatterns Transferred to Hydrogels for Designed Multivalent Carbohydrate–Lectin Interactions across Length Scales

et al. 2023

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Multivalent interactions between carbohydrates and proteins enable a broad range of selective chemical processes of critical biological importance. Such interactions can extend from the macromolecular scale (1−10 nm) up to much larger scales across a cell or tissue, placing substantial demands on chemically patterned materials aiming to leverage similar interactions in vitro.Here, we show that diyne amphiphiles with carbohydrate headgroups can be assembled on highly oriented pyrolytic graphite (HOPG) to generate nanometer-resolution carbohydrate patterns, with individual linear carbohydrate assemblies up to nearly 1 μm, and microscale geometric patterns. These are then photopolymerized and covalently transferred to the surfaces of hydrogels. This strategy suspends carbohydrate patterns on a relatively rigid polydiacetylene (persistence length ∼ 16 nm), exposed at the top surface of the hydrogel above the bulk pore structure. Transferred patterns of appropriate carbohydrates (e.g., N-acetyl-D-glucosamine, GlcNAc) enable selective, multivalent interactions (K D ∼ 40 nM) with wheat germ agglutinin (WGA), a model lectin that exhibits multivalent binding with appropriately spaced GlcNAc moieties. WGA binding affinity can be further improved (K D ∼ 10 nM) using diacetylenes that shift the polymer backbone closer to the displayed carbohydrate, suggesting that this strategy can be used to modulate carbohydrate presentation at interfaces. Conversely, GlcNAc-patterned surfaces do not induce specific binding of concanavalin A, and surfaces patterned with glucuronic acid, or with simple carboxylic acid or hydroxyl groups, do not induce WGA binding. More broadly, this approach may have utility in designing synthetic glycan−mimetic interfaces with features from molecular to mesoscopic scales, including soft scaffolds for cells.

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Binding of synthetic carbohydrate receptors to enveloped virus glycans: Insights from molecular dynamics simulations

Cited by 2 publications

References 35 publications

Molecular Engineering of Carbohydrate Recognition

Molecular Engineering of Carbohydrate Recognition

Surface-Templated Glycopolymer Nanopatterns Transferred to Hydrogels for Designed Multivalent Carbohydrate–Lectin Interactions across Length Scales

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