Rhodium‐Catalyzed Boron Arylation of 1,2‐Azaborines

Rudebusch, Gabriel E.; Zakharov, Lev N.; Liu, Shih‐Yuan

doi:10.1002/ange.201304443

Cited by 20 publications

(3 citation statements)

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“…In the first part of this article, we will describe a multi-gram scale synthesis of N-TBS-B-Cl-1,2-azaborine (3) using standard air-free techniques. This compound serves as a versatile intermediate that can be further functionalized to structurally more complex molecules 14,15 . Starting from 3, the synthesis and purification of N-H-B-ethyl-1,2-azaborine (5) for use in protein binding studies will be described.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Lee

Liu

2017

JoVE

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We describe a general synthesis of 1,2-azaborines using standard air-free techniques and protein complex preparation with T4 lysozyme mutants by vapor diffusion. Oxygen- and moisture-sensitive compounds are prepared and isolated under an inert atmosphere (N2) using either a vacuum gas manifold or a glove box. As an example of azaborine synthesis, we demonstrate the synthesis and purification of the volatile N-H-B-ethyl-1,2-azaborine by a five-step sequence involving distillation and column chromatography for the isolation of products. T4 lysozyme mutants L99A and L99A/M102Q are expressed with Escherichia coli RR1 strain. Standard protocols for chemical cell lysis followed by purification using carboxymethyl ion exchange column affords protein of sufficiently high purity for crystallization. Protein crystallization is performed in various concentrations of precipitant at different pH ranges using the hanging drop vapor diffusion method. Complex preparation with the small molecules is carried out by vapor diffusion method under an inert atmosphere. X-ray diffraction analysis of the crystal complex provides unambiguous structural evidence of binding interactions between the protein binding site and 1,2-azaborines.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Lee

Liu

2017

JoVE

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show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Lee

Liu

2017

JoVE

View full text Add to dashboard Cite

We describe a general synthesis of 1,2-azaborines using standard air-free techniques and protein complex preparation with T4 lysozyme mutants by vapor diffusion. Oxygen-and moisture-sensitive compounds are prepared and isolated under an inert atmosphere (N 2 ) using either a vacuum gas manifold or a glove box. As an example of azaborine synthesis, we demonstrate the synthesis and purification of the volatile N-H-B-ethyl-1,2-azaborine by a five-step sequence involving distillation and column chromatography for the isolation of products. T4 lysozyme mutants L99A and L99A/M102Q are expressed with Escherichia coli RR1 strain. Standard protocols for chemical cell lysis followed by purification using carboxymethyl ion exchange column affords protein of sufficiently high purity for crystallization. Protein crystallization is performed in various concentrations of precipitant at different pH ranges using the hanging drop vapor diffusion method. Complex preparation with the small molecules is carried out by vapor diffusion method under an inert atmosphere. X-ray diffraction analysis of the crystal complex provides unambiguous structural evidence of binding interactions between the protein binding site and 1,2-azaborines.

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“…The chemical structures within this paper resemble the NSAID Felbinac (biphenylylacetic acid) and replacement of the carboxylic acid of Felbinac and related derivatives may be of interest to the wider community. As an aside, one of the phenyl rings of Felbinac has been replaced with a BN bioisostere using rhodium-catalysed arylation chemistry [10]. TZDs (also termed glitazones) have been shown to reduce insulin resistance [11], concurring with a rise in glucose disposal and reduced hepatic glucose production.…”

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confidence: 99%

Unearthing Novel Thiazolidinone Building Blocks As Carboxylic Acid Bioisosteres

Scanlon

Wren

2020

Future Med. Chem.

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Aim: Thiazolidinones were prepared as building blocks for the replacement of carboxylic acids. Materials & methods: Chemical syntheses of thiazolidinones were developed. In addition, the drug-likeness of the target compounds was evaluated in silico. Results: The prepared compounds included the novel structure 4; 5-(3-Iodophenylmethylene)-2,4-thiazolidinedione. Conclusion: Exploration of the methods required to synthesize thiazolidinone building blocks was completed. This work allows future generation of bioisosteric analogs of drugs.

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Rhodium‐Catalyzed Boron Arylation of 1,2‐Azaborines

Cited by 20 publications

References 50 publications

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Unearthing Novel Thiazolidinone Building Blocks As Carboxylic Acid Bioisosteres

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