22 research outputs found

    7,7′-(3,3′-Dibenzyl-3H,3′H-4,4′-bi-1,2,3-triazole-5,5′-di­yl)bis­(4-methyl-2H-chromen-2-one)

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    The title compound, a bis-5,5′-triazole, C38H28N6O4, was observed as a side-product from the Sharpless–Meldal click reaction of the corresponding coumarin alkyne and benzyl­azide. Although the compound was present as a minor component, it crystallized in preference to the major product. The two triazole rings are almost orthogonal to each other [dihedral angle = 83.8 (1)°]. However the 4 and 4′ coumarin systems are close to coplanar with their respective triazole rings [23.6 (1) and 15.1 (1)°]. Each of the benzene rings packs approximately face-to-face with the opposing coumarin ring systems, with inter­planar angles of 7.7 (1) and 25.3 (1)° and distances of 3.567 (2) and 3.929 (2) Å between the respective centroids of the opposing rings

    Towards Equitable, Diverse, and Inclusive science collaborations: The Multimessenger Diversity Network

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    5-(1-Benzyl-1 H

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    5-(4-Hexyl-1 H

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    Detection of Cellular Sialic Acid Content Using Nitrobenzoxadiazole Carbonyl-Reactive Chromophores

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    The selective ligation of hydrazine and amino-oxy compounds with carbonyls has gained popularity as a detection strategy with the recognition of aniline catalysis as a way to accelerate the labeling reaction in water. Aldehydes are a convenient functional group choice since there are few native aldehydes found at the cell surface. Aldehydes can be selectively introduced into sialic acid containing glycoproteins by treatment with dilute sodium periodate. Thus, the combination of periodate oxidation with aniline-catalyzed ligation (PAL) has become a viable method for detection of glycoconjugates on live cells. Herein we examine two fluorescent nitrobenzoxadiazole dyes for labeling of glycoproteins and cell surface glycoconjugates. We introduce a novel 4-aminooxy-7-nitro-benz-[2,1,3-<i>d</i>]-oxadiazole (NBDAO) (<b>5</b>) fluorophore, and offer a comparison to commercial dyes including the known 4-hydrazino-7-nitro-benz-[2,1,3-<i>d</i>]-oxadiazole (NBDH) (<b>2</b>) and Bodipy FL hydrazide. We confirm specificity for sialic acid moieties and that both dyes are suitable for in vitro and in vivo labeling studies using PAL and fluorescence spectroscopy. The dyes examined here are attractive labeling agents for microscopy, as they can be excited by a 488 nm laser line and can be made in a few synthetic steps. These carbonyl-reactive chromophores provide a one step alternative to avidin–biotin labeling strategies and simplify the detection of sialic acid in cells and glycoproteins
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