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Chemical Structure| 620-23-5 Chemical Structure| 620-23-5
Chemical Structure| 620-23-5

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m-Tolualdehyde (3-Methylbenzaldehyde) is an aromatic aldehyde commonly used as an intermediate in organic synthesis and as a food additive.

Synonyms: 3-Methylbenzaldehyde

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Product Citations

Product Citations      Show More

Lu, Yen-Chu ; Adukure, Ronald D ; Roy, Satyajit ; Chien, Derek L ; McGill, Matthew J ; Polara, Sarthi , et al.

Abstract: Hydrogen atom transfer (HAT) constitutes a powerful mechanism exploited in biology and chemistry to functionalize ubiquitous C(sp3)−H bonds in organic molecules. Despite its synthetic potential, achieving stereocontrol in chemical HAT-mediated C−H functionalization transformations remains challenging. By merging the radical reactivity of thiamine (ThDP)-dependent enzymes with chemical hydrogen atom transfer, we report here a photobiocatalytic strategy for the enantioselective C(sp3)−H acylation of an organic substrate, a transformation not found in nature nor currently attainable by chemical means. This method enables the direct functionalization of benzylic C(sp3)−H sites in a broad range of substrates to furnish valuable enantioenriched ketone motifs with good to high enantioselectivity (up to 96% ee). Mechanistic and spectroscopic studies support the involvement of radical species derived from the Breslow intermediate and C−H substrate, highlight the critical role of the photocatalyst and hydrogen atom abstraction reagents for productive catalysis, and reveal a specific enzyme/photocatalyst interaction favoring single electron transfer during catalysis. Further insights into how the enantioselectivity of the C−C bond-forming reaction is controlled by the enzyme and influenced by active site mutations were gained via molecular modeling. This study illustrates the productive integration of ThDP-mediated biocatalysis with chemical HAT, expanding the range of asymmetric C(sp3)−H functionalization transformations that can be accessed through biocatalysis.

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Shifali Shishodia ; Raymundo Nuñez ; Brayden P. Strohmier ; Karina L. Bursch ; Christopher J. Goetz ; Michael D. Olp , et al.

Abstract: PBRM1 is a subunit of the PBAF chromatin remodeling complex that uniquely contains six bromodomains. PBRM1 can operate as a tumor suppressor or tumor promoter. PBRM1 is a tumor promoter in prostate cancer, contributing to migratory and immunosuppressive phenotypes. Selective chemical probes targeting PBRM1 bromodomains are desired to elucidate the association between aberrant PBRM1 chromatin binding and cancer pathogenesis and the contributions of PBRM1 to immunotherapy. Previous PBRM1 inhibitors unselectively bind SMARCA2 and SMARCA4 bromodomains with nanomolar potency. We used our protein-detected NMR screening pipeline to screen 1968 fragments against the second PBRM1 bromodomain, identifying 17 hits with Kd values from 45 μM to >2 mM. Structure–activity relationship studies on the tightest-binding hit resulted in nanomolar inhibitors with selectivity for PBRM1 over SMARCA2 and SMARCA4. These chemical probes inhibit the association of full-length PBRM1 to acetylated histone peptides and selectively inhibit growth of a PBRM1-dependent prostate cancer cell line.

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Product Details of m-Tolualdehyde

CAS No. :620-23-5
Formula : C8H8O
M.W : 120.15
SMILES Code : O=CC1=CC=CC(C)=C1
Synonyms :
3-Methylbenzaldehyde
MDL No. :MFCD00003374
InChI Key :OVWYEQOVUDKZNU-UHFFFAOYSA-N
Pubchem ID :12105

Safety of m-Tolualdehyde

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of m-Tolualdehyde

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 620-23-5 ]
  • Downstream synthetic route of [ 620-23-5 ]

[ 620-23-5 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 620-23-5 ]
  • [ 1082041-78-8 ]
References: [1] Patent: WO2012/35078, 2012, A1, .
[2] Patent: US2014/45872, 2014, A1, .
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 789 - 801.
 

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