Evaluation of novel fluorescence probes for conjugation purposes using the traceless Staudinger Ligation

Wodtke, Robert; König, Jonas; Pigorsch, Arne; Köckerling, Martin; Mamat, Constantin

doi:10.1016/j.dyepig.2014.08.022

Cited by 15 publications

(11 citation statements)

References 51 publications

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“…NMR spectra of all compounds were recorded on an Agilent DD2-400 MHz or DD2-600 MHz NMR spectrometer with ProbeOne. Chemical shis of the 1 H, 19 F, and 13 C spectra were reported in parts per million (ppm) using TMS as internal standard for 1 H/ 13 C and CFCl 3 for 19 F spectra at 25 C unless otherwise stated. Spectra were calibrated to their solvent signals.…”

Section: Generalmentioning

confidence: 99%

“…for polymerizations. 18 Furthermore, piperazines are also in use for the synthesis of labeling compounds and building blocks, e.g., for inserting uorescent dyes 19,20 or for the introduction of radionuclides [21][22][23] into biologically active molecules. The understanding of the conformational behavior of these functionalized piperazines is important not only to explain biological and/or pharmacological effects, but also for applications in material sciences.…”

Section: Introductionmentioning

confidence: 99%

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NMR-based investigations of acyl-functionalized piperazines concerning their conformational behavior in solution

et al. 2018

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Section: Generalmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

NMR-based investigations of acyl-functionalized piperazines concerning their conformational behavior in solution

et al. 2018

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“…For this purpose, the azide-containing building block 5b was reacted with 8 [30] to give 9 . The resulting reference compound 9 was obtained after 3 h reaction time in a high yield of 76%.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

Mamat

Pretze

Gott

et al. 2016

Beilstein J. Org. Chem.

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Novel, functionalized piperazine derivatives were successfully synthesized and fully characterized by 1H/13C/19F NMR, MS, elemental analysis and lipophilicity. All piperazine compounds occur as conformers resulting from the partial amide double bond. Furthermore, a second conformational shape was observed for all nitro derivatives due to the limited change of the piperazine chair conformation. Therefore, two coalescence points were determined and their resulting activation energy barriers were calculated using 1H NMR. To support this result, single crystals of 1-(4-nitrobenzoyl)piperazine (3a, monoclinic, space group C2/c, a = 24.587(2), b = 7.0726(6), c = 14.171(1) Å, β = 119.257(8)°, V = 2149.9(4) Å3, Z = 4, D obs = 1.454 g/cm3) and the alkyne derivative 4-(but-3-yn-1-yl)-1-(4-fluorobenzoyl)piperazine (4b, monoclinic, space group P21/n, a = 10.5982(2), b = 8.4705(1), c = 14.8929(3) Å, β = 97.430(1)°, V = 1325.74(4) Å3, Z = 4, D obs = 1.304 g/cm3) were obtained from a saturated ethyl acetate solution. The rotational conformation of these compounds was also verified by XRD. As proof of concept for future labeling purposes, both nitropiperazines were reacted with [18F]F–. To test the applicability of these compounds as possible 18F-building blocks, two biomolecules were modified and chosen for conjugation either using the Huisgen-click reaction or the traceless Staudinger ligation.

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“…For a general introduction to the chemistry and radiochemistry of benzoate functionalized 2-(diphenylphosphanyl)phenol derivatives, see: Mamat et al (2009); Pretze et al (2010). For applications of chloromethyl and hydroxymethyl benzoates, see: Mamat et al (2011); Wodtke et al (2015 Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of 2-(diphenylphosphanyl)phenyl 4-(hydroxymethyl)benzoate

Mamat¹,

Flemming

Köckerling

2014

Acta Cryst E

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The title compound, C26H21O3P, was obtained as by-product due to the hydrolysis of the desired tosylated compound. The dihedral angles between the three aromatic rings attached to the P atom lie in the range 78.1 (1)–87.6 (1)°. The hydroxymethyl group is disordered between two conformations in a 0.719 (9):0.281 (9) ratio. The hydroxy H atom is not involved in intermolecular interactions, while the hydroxy O atom serves as a donor for weak C—H⋯O hydrogen bonds, which link the molecules into chains propagating in [0-11].

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Evaluation of novel fluorescence probes for conjugation purposes using the traceless Staudinger Ligation

Cited by 15 publications

References 51 publications

NMR-based investigations of acyl-functionalized piperazines concerning their conformational behavior in solution

NMR-based investigations of acyl-functionalized piperazines concerning their conformational behavior in solution

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

Crystal structure of 2-(diphenylphosphanyl)phenyl 4-(hydroxymethyl)benzoate

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