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Chemical Structure| 15086-94-9 Chemical Structure| 15086-94-9
Chemical Structure| 15086-94-9

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Synonyms: Acid Red 87 free base

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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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Ben-Zvi, Benjamin ;

Abstract: The ability to modify DNA and functionalize proteins is a foundational tool in chemical biology, essential for probing complex biological systems and for engineering new or improvedfunctions at the molecular level. Such modifications enable researchers to track, visualize, and manipulate biomolecules of interest, enabling the development of targeted therapeutics, biosensors, and diagnostic assays. Photoredox chemistry, which operates under mild conditions and leverages light to achieve high spatiotemporal control, provides a powerful and biocompatible platform for these transformations in biologically relevant settings. The use of lower energy light, such as red or near-infrared light, further enhances this approach by minimizing phototoxicity and allowing deeper tissue penetration. These features make red-shifted photocatalysis an ideal platform for bioorthogonal modifications, expanding the toolkit for probing and manipulating biological systems. Towards this goal, this dissertation describes the use of innovative photocatalytic methods to modify and functionalize biologically relevant macromolecules. The research presented here describes the use of novel diazonium compounds along with red-shifted, low-energy light to perform modifications on DNA and proteins. The development of novel photoactivatable multi-diazonium compounds led to the effective and potent degradation of DNA under mild conditions utilizing only low energy light. The potency of this method was comparable to those of its natural counterparts, such as calicheamicin. Diazonium compounds offer a synthetically more accessible mimic of natural enediyne-containing DNA cleaving agents. This method provides a more cost-effective, efficient, and modular alternative to enediynes derivatives and offers the potential for enhanced specificity through spatiotemporal control. The photoactivatable nature of diazonium compounds was also harnessed for the photocatalytic labeling of proteins. “TagC-RED,” a Retro-Ene type sigmatropic rearrangement of Diazonium compounds for Cysteine-specific tagging, activated by near-infrared light (λ > 1000 nm), is also introduced and detailed in this report. TagC-RED is rapid, catalyst-free, compatible in cellular environments, and capable of penetrating tissues, making it suitable for intracellular labeling. This method holds significant potential as a platform for targeted protein labeling and real-time tracking of cellular processes. In parallel, foundational efforts to enable the specific spatiotemporal labeling of target sites on polynucleotides are also detailed here. Instead of the diazonium-mediated method used for light-controlled and site-selective labeling in proteins, DNA_x005f_x0002_photocatalyst chimera complexes were synthesized and designed to achieve site-selective modification of polynucleotides. Preliminary results demonstrated that each component of these photocatalyst-DNA chimera complexes retained its functional integrity: the photocatalyst maintained catalytic activity and the DNA retained hybridization capability. This emerging technology can address the long-standing challenge of site-specific DNA and RNA modification, enabling the photocatalytic incorporation of diverse natural and synthetic functional groups for the study of polynucleotide structure, dynamics, function, and therapeutic targeting.

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Davis, Katherine ; Lippincott, Leon ; Malenius, Danielle ; Saleem, Rida ; Majeed, Saman ;

Abstract: Xylazine, an α2-adrenergic agonist approved exclusively for veterinary use, has recently emerged as a widespread adulterant in illicit opioid supplies, particularly fentanyl. Its presence poses significant public health risks, including profound sedation, necrotic skin ulcers, and the lack of an effective antidote. Despite its growing implication in overdose cases, presumptive testing methods for xylazine remain underdeveloped in forensic and public health settings. This study addresses the urgent need for reliable screening tools by evaluating the applicability of chemical spot tests, microcrystalline tests, and commercially available xylazine immunoassay test strips and field drug test kits. A comprehensive panel of chemical reagents was tested, and crystal morphology was assessed using light microscopy and scanning electron microscopy (SEM). Among the colorimetric reagents examined, Cobalt thiocyanate, (pH 7.0), Liebermann, Mandelin, Mecke, Marquis, Scott, and Young reagents produced distinct and rapid color changes with xylazine. Gold chloride yielded reproducible, well-defined microcrystals across xylazine formulations, establishing it as the most effective reagent for microcrystalline testing. All XTS yielded true positives with xylazine; however, many commercial and on-site screening tools displayed cross-reactivity or false-positive results, raising concerns about their specificity and reliability. These findings highlight the need to develop and validate xylazine-specific presumptive tests to enhance forensic investigations, support harm reduction efforts, and enable more informed, safer decision-making by people who use drugs.

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Product Details of Eosin Y

CAS No. :15086-94-9
Formula : C20H8Br4O5
M.W : 647.89
SMILES Code : O=C1OC2(C3=C(OC4=C2C=C(Br)C(O)=C4Br)C(Br)=C(O)C(Br)=C3)C5=C1C=CC=C5
Synonyms :
Acid Red 87 free base
MDL No. :MFCD00036189
InChI Key :DBZJJPROPLPMSN-UHFFFAOYSA-N
Pubchem ID :27020

Safety of Eosin Y

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338
 

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