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Rapid Structure Determination of Bioactive 4''-tetrahydrofurfuryl Macrozone Reaction Mixture Components by LC/SPE/Cryo NMR and MS

Habinovec, Iva; Mikulandra, Ivana; Sekula, Lucia Ema; Gašperov, Jana; Kazazić, Saša; Novak, Predrag (2021) Rapid Structure Determination of Bioactive 4''-tetrahydrofurfuryl Macrozone Reaction Mixture Components by LC/SPE/Cryo NMR and MS. Molecules, 26 (6316). ISSN 1420-3049

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Abstract

LC-SPE/cryo NMR and MS methodologies have been developed and employed for a rapid structure determination of 4″-tetrahydrofurfuryl macrozone reaction mixture components. Macrozones, novel conjugates of azithromycin, and thiosemicarbazones have shown very good in vitro antibacterial activities against susceptible and some resistant bacterial strains and are promising agents for further development. The post-column multiple trapping of the chromatographically separated reaction mixture components on the SPE cartridges increased the sensitivity and together with cryogenically cooled NMR probe made it possible to identify and structurally characterize main 4″- tetrahydrofurfuryl macrozone reaction mixture compounds including those present at very low concentration level. This approach has several advantages over a classical off-line procedure, efficiency and low solvent consumption being the two most important ones. All identified components were process-related. It has been demonstrated that two different kinds of compounds with respect to structure were identified, i.e., macrolide- related and thiosemicarbazone-related ones. This methodology can serve as a platform for reliable and effective macrolides reaction components structure profiling, serving as both isolation and identification tools.

Item Type: Article
Uncontrolled Keywords: azithromycin conjugates ; macrozones ; HPLC-SPE/cryo NMR ; MS ; structure determination
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Physical Chemistry
Projects:
Project titleProject leaderProject codeProject type
Makrozoni, novi konjugati makrolidnih antibiotika: Dizajn, priprava i interakcijeNovak, PredragIP-2018-01-8098HRZZ
Depositing User: Sofija Konjević
Date Deposited: 12 Nov 2021 13:58
URI: http://fulir.irb.hr/id/eprint/6670
DOI: 10.3390/molecules26206316

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