Suzuki homo-coupling reaction based fluorescent sensors for monosaccharides

Xu, Suying; Wang, Hui‐Chen; Flower, Stephen E.; Fossey, John S.; Jiang, Yun‐Bao; James, Tony D.

doi:10.1039/c4ra07331b

Cited by 12 publications

(13 citation statements)

References 18 publications

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“…The co-authors of this report have investigated triazoles as chemosensors 51 − 53 and as products of asymmetric synthesis. 54 − 58 Furthermore, an interest in boronic acid derivatives as chemosensors, 59 − 64 including the use of cross-coupling reactions as a means of sensing, 65 means the co-authors of this report are familiar with boronic acids and esters. 66 As such, a desire to bring together these streams of research under one umbrella has led to the research reported in this manuscript.…”

Section: Introductionmentioning

confidence: 99%

Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling

et al. 2018

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Twelve 1,5-disubtituted and fourteen 5-substituted 1,2,3-triazole derivatives bearing diaryl or dialkyl phosphines at the 5-position were synthesized and used as ligands for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions. Bulky substrates were tested, and lead-like product formation was demonstrated. The online tool SambVca2.0 was used to assess steric parameters of ligands and preliminary buried volume determination using XRD-obtained data in a small number of cases proved to be informative. Two modeling approaches were compared for the determination of the buried volume of ligands where XRD data was not available. An approach with imposed steric restrictions was found to be superior in leading to buried volume determinations that closely correlate with observed reaction conversions. The online tool LLAMA was used to determine lead-likeness of potential Suzuki–Miyaura cross-coupling products, from which 10 of the most lead-like were successfully synthesized. Thus, confirming these readily accessible triazole-containing phosphines as highly suitable ligands for reaction screening and optimization in drug discovery campaigns.

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Section: Introductionmentioning

confidence: 99%

Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling

et al. 2018

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“…Such a species has been described in the literature to be formed as a part of the homocoupling process, and it has been assumed that the material in hand is that reported. 33…”

Section: Resultsmentioning

confidence: 99%

Active Palladium Colloids via Palladacycle Degradation as Efficient Catalysts for Oxidative Homocoupling and Cross-Coupling of Aryl Boronic Acids

et al. 2017

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Active palladium colloids formed upon degradation of a palladacyclic complex (Herrmann–Beller 1 ) have been isolated for the first time and thoroughly characterized with techniques such as transmission electron microscopy (TEM), high-resolution TEM, X-ray photoelectron spectroscopy (XPS), and extended X-ray absorption fine structure spectroscopy. The synthesized palladium colloids have been utilized as efficient catalysts for the oxidative homocoupling of aryl boronic acids. Cross-coupling of two different aryl boronic acids has also been made possible using these active palladium colloids. This is the first report of this kind of coupling between aryl boronic acids.

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“…Davis et al [2,[26][27][28][29] proposed different biomimetic receptors for carbohydrates known as synthetic lectins. Jiang et al [30][31][32][33] proposed simple boronic acids and their aggregates for saccharide sensing. However, the receptors have their disadvantages.…”

Section: Motivationmentioning

confidence: 99%

A Machine Learning Prediction Model for the Affinity Between Glucose and Binder

Kondabala¹,

Kumar²,

Ali³

2019

RIA

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The glucose is an important source of fuel for the body. The binding affinity is an essential indicator of the interaction of a glucose molecule with its binder. This paper proposes a novel machine learning model for predicting the binding affinity of a small glucose molecule with the binder. Seven regression algorithms were compared on a dataset is generated based on Molecular Mechanics-Generalized Born and Surface Area (MM-GBSA). Through the comparison, Random Forest and Decision Tree were selected for our model, in light of their robustness and accuracy. The established model predicts binding affinity from the interaction properties of compounds and glucose, which are obtained through GLIDE program from Schrödinger software suite 2018-4. Finally, the prediction accuracy of our model was confirmed through k-fold cross-validation. Our research provides an efficient and low-cost method for screening of molecules during the development of glucose binders.

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Suzuki homo-coupling reaction based fluorescent sensors for monosaccharides

Cited by 12 publications

References 18 publications

Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling

Phosphino-Triazole Ligands for Palladium-Catalyzed Cross-Coupling

Active Palladium Colloids via Palladacycle Degradation as Efficient Catalysts for Oxidative Homocoupling and Cross-Coupling of Aryl Boronic Acids

A Machine Learning Prediction Model for the Affinity Between Glucose and Binder

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