Synthesis of sugar oxime ether surfactants

Ewan, Harrison S.; Muli, Christine S.; Touba, Steven; Bellinghiere, Amy T.; Veitschegger, Anne M.; Smith, Travis B.; Pistel, William L.; Jewell, William T.; Rowe, Rebecca K.; Hagen, John P.; Palandoken, Hasan

doi:10.1016/j.tetlet.2014.07.036

Cited by 16 publications

(10 citation statements)

References 26 publications

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“…[117,118] Oximes are an important class of molecules present in the precursor of Nylon 6 [119] and several important surfactants as well. [120][121][122][123] Because of the high interaction between the non-Scheme 13. Pyrimidine-assistance for diverse CÀ H functionalization of anilines derivatives.…”

Section: Monodentate N-based Groupsmentioning

confidence: 99%

Decoding Directing Groups and Their Pivotal Role in C−H Activation

Murali

Machado

Carvalho

et al. 2021

Chemistry A European J

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Section: Monodentate N-based Groupsmentioning

confidence: 99%

Decoding Directing Groups and Their Pivotal Role in C−H Activation

Murali

Machado

Carvalho

et al. 2021

Chemistry A European J

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“…Inspired by common glycan labelling strategies, reviewed in Ref. 25, three reactive handles were chosen: hydroxylamine, [41][42][43][44] hydrazide, [45] and 2-aminobenzamide (2-AB). [46][47][48] Five unique LALDI tags were synthesised, combining the two selected LDI enhancers 3 and 4 and the three reactive handles through their solubilising linker (compounds 5-9, Table 2).…”

Section: Development Of Laldi Tags For Reducing Carbohydratesmentioning

confidence: 99%

Pyrene Tags for the Detection of Carbohydrates by Label‐Assisted Laser Desorption/Ionisation Mass Spectrometry**

et al. 2021

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Matrix-assisted laser desorption/ionisation mass spectrometry (MALDI-MS) is widely used for the analysis of biomolecules. Label-assisted laser desorption/ionisation mass spectrometry (LALDI-MS) is a matrix-free variant of MALDI-MS, in which only analytes covalently attached to a laser desorption/ionisation (LDI) enhancer are detected. LALDI-MS has shown promise in overcoming the limitations of MALDI-MS in terms of sample preparation and MS analysis. In this work, we have developed a series of pyrene-based LDI reagents (LALDI tags) that can be used for labelling and LALDI-MS analysis of reducing carbohydrates from complex (biological) samples without the need for additional chemical derivatisation or purification. We have systematically explored the suitability of four pyrene-based LDI enhancers and three aldehyde-reactive handles, optimised sample preparation, and demonstrated the use of LALDI tags for the detection of lactose. We have also exemplified the potential of LALDI tags for labelling carbohydrates in biological samples by direct detection of lactose in cow's milk. These results demonstrate that LALDI-MS is a promising technique for the analysis of reducing carbohydrates in biological samples, and pave the way for the development of LALDI-MS for glycomics and diagnostics.

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“…To label reducing carbohydrates, such as N-or O-glycans released through enzymatic 37,38 or chemical cleavage techniques, 39,40 suitable reactive handles were required that would be efficient, selective, and form a stable conjugate product in the presence of a complex biological matrix. Inspired by common glycan labelling strategies, reviewed in 25 , three reactive handles were chosen: hydroxylamine, [41][42][43][44] hydrazide, 45 and 2-aminobenzamide (2-AB). [46][47][48] Five unique LALDI tags were synthesised, combining the two selected LDI enhancers 3 and 4 and the three reactive handles through their solubilising linker (compounds 5-9, Table 2).…”

Section: Development Of Laldi Tags For Reducing Carbohydratesmentioning

confidence: 99%

Water-Soluble Pyrene Tags Enable the Detection of Carbohydrates by Label-Assisted Laser Desorption/ionisation Mass Spectrometry

Hauser¹,

Bergström²,

Kulak³

et al. 2020

Preprint

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<div>Matrix-assisted laser desorption/ionisation mass spectrometry (MALDI-MS) is widely used for the</div><div>analysis of biomolecules. Label-assisted laser desorption/ionisation mass spectrometry (LALDI-MS) is</div><div>a matrix-free variant of MALDI-MS, in which only analytes covalently attached to a laser</div><div>desorption/ionisation (LDI) enhancer are detected. LALDI-MS has shown promise in overcoming</div><div>limitations of MALDI-MS in terms of sample preparation and MS analysis. In this work, we have</div><div>developed water-soluble pyrene-based LDI reagents (LALDI tags) that can be used for (in situ) labelling</div><div>and LALDI-MS analysis of reducing carbohydrates from complex (biological) samples without the need</div><div>for additional chemical derivatisation or purification. We have systematically explored the suitability</div><div>of four pyrene-based LDI enhancers and three aldehyde-reactive handles, optimised sample</div><div>preparation, and exemplified the use of a LALDI tag by the detection of lactose in cow’s milk. These</div><div>results demonstrate that LALDI-MS is a promising technique for the analysis of reducing carbohydrates</div><div>in biological samples, and pave the way for the development of LALDI-MS for glycomics and</div><div>diagnostics.</div>

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Synthesis of sugar oxime ether surfactants

Cited by 16 publications

References 26 publications

Decoding Directing Groups and Their Pivotal Role in C−H Activation

Decoding Directing Groups and Their Pivotal Role in C−H Activation

Pyrene Tags for the Detection of Carbohydrates by Label‐Assisted Laser Desorption/Ionisation Mass Spectrometry**

Water-Soluble Pyrene Tags Enable the Detection of Carbohydrates by Label-Assisted Laser Desorption/ionisation Mass Spectrometry

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