Naslov
Sinteza (±)‐trans‐3‐amino‐β‐laktama i njegova enantioseparacija na novoj polisaharidnoj kiralnoj stacionarnoj fazi HPLC‐om i SFC‐om
(Synthesis of (±)‐trans‐3‐amino‐β‐lactam and its enantioseparation on the new polysaccharide‐based chiral stationary phase by HPLC and SFC)

Autori
Jurin, Mladenka ; Kontrec, Darko ; Roje, Marin

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
26th Croatian Meeting of Chemists and Chemical Engineers : Book of Abstracts / - , 2019, 132-132

Skup
26. hrvatski skup kemičara i kemijskih inženjera (26HSKIKI) ; 4. simpozij Vladimir Prelog

Mjesto i datum
Šibenik, Hrvatska, 09.04.2019. - 12.04.2019

Vrsta sudjelovanja
Poster

Vrsta recenzije
Domaća recenzija

Ključne riječi
β‐Lactami ; SFC ; HPLC

Sažetak
β‐Lactams, or azetidin‐2‐ones, are of utmost importance in medicine owing to their broad range of bioactivities [1]. They are the key structural component in the most widely used class of antibiotics, β-lactam antibiotics, such as penicillin, cephalosporin, carbapenem, etc [2]. Apart from their pharmacological purposes, β‐lactams are also valuable from a synthetic point of view as they can function as building blocks for the synthesis of numerous biologically active and natural compounds [1]. Some of the example include non-natural amino acid, peptides and peptidomimetics, anti-cancer drug paclitaxel and other taxis and anti-tumor antibiotics lankacidin [3]. β-lactam can easily rearranged into five-membered, six-membered, medium-size rings, which is in focus of our current research [4] In conducted research the (±)-trans-3-amino-β-lactam 3 was prepared by Staudinger reaction, [2+2] ketene-imine cycloaddition. Reaction of imine 1 with N-phthaloylglycine in the presence of base triethylamine and 2-chloro-N-methylpyridinium iodide in dry dichloromethane afforded a mixture of (±)-cis 2a and (±)-trans-3-phthalimido-β-lactam 2b in a ratio 1:5 (Scheme 1). In the next step, deprotection of the phthalimido group was carried out by converting the (±)-trans-2b to 3-amino-β-lactam 3 with ethylene diamine in dry ethanol (Scheme 2). The stereochemistry of β-lactams has already been determined and remains unchanged during this conversion [4]. Enantioseparation of 3 was studied using HPLC and SFC on the new chiral stationary phase based on a very unique polysaccharide, and also on the "golden four" polysaccharide type chiral stationary phases. The obtained results showed that the enantioseparation of 3 achieved by SFC is superior in terms of high resolution and short analysis time than using conventional HPLC.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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