Click chemistry is used to functionalize simple lipophilic and water-soluble molecules, a complex PEGylated phospholipid (DSPE-PEG2000), and two benzylic substrates with the 2-(hydroxyimino)aldehyde (HIA) group. To this end, two terminal alkynes bearing the HIA moiety were synthesized and coupled to different azides through copper(I)-catalyzed azide alkyne cycloaddition (CuAAC). Norrish–Yang photoisomerization (λ= 365 nm, LED source) is successfully obtained, with no interference by the triazole linker, except when the forbidden n-π* carbonyl transition is screened by a remote substituent such as salicylaldehyde. UV-Vis spectrometry suggests a specific interaction of HIAs with Cu(II), whereas no such evidence is found with Cu(I). We thereby show that the CuAAC methodology can be used successfully to obtain HIA-based UV-responsive hydrophilic or lipophilic ligands, phospholipidic components for the construction of liposomes, and macrocycle precursors. © 2020 Wiley-VCH GmbH

Click-connected 2-(hydroxyimino)aldehydes for the design of UV-responsive functional molecules / D’Acunzo, Francesca; Carbonaro, Linda; Dalla Cort, Antonella; Di Sabato, Antonio; Filippini, Dario; Leonelli, Francesca; Mancini, Laura; Gentili, Patrizia. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - 2021:2(2021), pp. 289-294. [10.1002/ejoc.202001303]

Click-connected 2-(hydroxyimino)aldehydes for the design of UV-responsive functional molecules

D’Acunzo, Francesca
;
Dalla Cort, Antonella
Membro del Collaboration Group
;
Di Sabato, Antonio
Membro del Collaboration Group
;
Filippini, Dario
Membro del Collaboration Group
;
Leonelli, Francesca;Mancini, Laura;Gentili,Patrizia
2021

Abstract

Click chemistry is used to functionalize simple lipophilic and water-soluble molecules, a complex PEGylated phospholipid (DSPE-PEG2000), and two benzylic substrates with the 2-(hydroxyimino)aldehyde (HIA) group. To this end, two terminal alkynes bearing the HIA moiety were synthesized and coupled to different azides through copper(I)-catalyzed azide alkyne cycloaddition (CuAAC). Norrish–Yang photoisomerization (λ= 365 nm, LED source) is successfully obtained, with no interference by the triazole linker, except when the forbidden n-π* carbonyl transition is screened by a remote substituent such as salicylaldehyde. UV-Vis spectrometry suggests a specific interaction of HIAs with Cu(II), whereas no such evidence is found with Cu(I). We thereby show that the CuAAC methodology can be used successfully to obtain HIA-based UV-responsive hydrophilic or lipophilic ligands, phospholipidic components for the construction of liposomes, and macrocycle precursors. © 2020 Wiley-VCH GmbH
2021
ciclobutanol oxime; click chemistry; 2-(hydroxyimino)aldehyde; photochemistry; LED
01 Pubblicazione su rivista::01a Articolo in rivista
Click-connected 2-(hydroxyimino)aldehydes for the design of UV-responsive functional molecules / D’Acunzo, Francesca; Carbonaro, Linda; Dalla Cort, Antonella; Di Sabato, Antonio; Filippini, Dario; Leonelli, Francesca; Mancini, Laura; Gentili, Patrizia. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - 2021:2(2021), pp. 289-294. [10.1002/ejoc.202001303]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/1479206
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