Exploiting Ligand and Receptor Adaptability in Rational Drug Design Using Dynamics and Structure-Based Strategies

LaPlante, Steven R.

doi:10.1007/128_2006_087

Cited by 8 publications

(2 citation statements)

References 93 publications

(151 reference statements)

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“…To assess the relative flexibility of the individual furanose rings, we determined 13 C spin lattice relaxation times ( T 1 ) for oligosaccharides 4 , 6 − 8 , and 11 as this data is a reasonable probe for molecules of this size . The resulting average NT 1 values of all carbons in each ring (with N being the number of protons attached to a particular carbon atom) are summarized in Table .…”

Section: Resultsmentioning

confidence: 99%

Ligand Specificity of CS-35, a Monoclonal Antibody That Recognizes Mycobacterial Lipoarabinomannan: A Model System for Oligofuranoside−Protein Recognition

et al. 2007

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The CS-35 antibody is widely used in the characterization of glycans containing D-arabinofuranose residues, in particular polysaccharides present in the mycobacterial cell wall. A detailed understanding of the combining site of this antibody and the measurement of its binding to different ligands is of interest as this knowledge will have implications in the characterization of arabinofuranose-containing glycoconjugates that are increasingly recognized as important biological molecules. Of even greater significance is that an in-depth study of this carbohydrate-protein interaction will provide insights into the mechanisms by which oligosaccharides containing furanose rings are bound by proteins, an area that has, to date, received little attention. This system has been refractory to X-ray crystallography, and thus we report here a study of the interaction of CS-35 with its ligands using a combination of chemical synthesis, mass spectrometry, titration microcalorimetry, and NMR spectroscopy. Through these investigations we have established that the binding pocket recognizes, as a minimum epitope, a linear tetrasaccharide motif and that the residues at the reducing and non-reducing end of the oligosaccharide are essential for tight binding. The residue at the non-reducing end appears to be bound in an aliphatic pocket, whereas the rest of the tetrasaccharide interacts more strongly with aromatic amino acids.

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Section: Resultsmentioning

confidence: 99%

Ligand Specificity of CS-35, a Monoclonal Antibody That Recognizes Mycobacterial Lipoarabinomannan: A Model System for Oligofuranoside−Protein Recognition

et al. 2007

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“…Adaptability is an omnipresent feature of the natural world. − For instance, to survive, all living beings have to respond to external stimuli, thus potentially turning disadvantages into advantages . In supramolecular chemistry, synthetic hosts that display guest-driven changes in structure allow a diversity in binding that extends beyond what might be expected for more preorganized systems that adhere to a strict interpretation of the lock and key principle. , …”

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confidence: 99%

Reversible Macrocycle-to-Macrocycle Interconversion Driven by Solvent Selection

et al. 2023

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Macrocycle-to-macrocycle interconversions are of interest because they can allow access to a variety of structures. However, reversible interconversion between different sized macrocycles remains challenging to control. Herein, we report a facile one-pot synthesis of a series of self-assembled macrocycles from readily prepared α,α′-linked oligopyrrolic dialdehydes and various alkyl diamines. The condensation of pyridine-bridged oligopyrrolic dialdehyde 3 and simple alkyl diamines proved independent of solvent, always yielding the [2 + 2] macrocyclic products. However, when 3 was condensed with 2,2′-oxybis(ethylamine) 14, either ([1 + 1] or [2 + 2]) products are obtained depending on the choice of solvent. Reaction of 3 and 14 in methanol, ethanol, or chloroform gave the [1 + 1] macrocycle as the sole product. In contrast, condensation of 3 and 14 in dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), or acetonitrile (MeCN) yielded the [2 + 2] macrocycle as the major product in the form of a precipitate. Reversible interconversion between the [1 + 1] and [2 + 2] macrocycles could be achieved by tuning the solvent, with the ratio driven by thermodynamic and solubility considerations.

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Microfluidic Devices for Studying Kinetics

Wilson

2010

Microfluidic Devices in Nanotechnology

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Exploiting Ligand and Receptor Adaptability in Rational Drug Design Using Dynamics and Structure-Based Strategies

Cited by 8 publications

References 93 publications

Ligand Specificity of CS-35, a Monoclonal Antibody That Recognizes Mycobacterial Lipoarabinomannan: A Model System for Oligofuranoside−Protein Recognition

Ligand Specificity of CS-35, a Monoclonal Antibody That Recognizes Mycobacterial Lipoarabinomannan: A Model System for Oligofuranoside−Protein Recognition

Reversible Macrocycle-to-Macrocycle Interconversion Driven by Solvent Selection

Microfluidic Devices for Studying Kinetics

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