Application of Biotechnology and Chiral Technology Methods in the Production of Ectoine Enantiomers

Šišić, Marcela; Jurin, Mladenka; Šimatović, Ana; Vujaklija, Dušica; Jakas, Andreja; Roje, Marin (2024) Application of Biotechnology and Chiral Technology Methods in the Production of Ectoine Enantiomers. Applied Sciences, 14 (18). ISSN 2076-3417

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Abstract

Natural ectoine, (+)-(4S)-2-methyl-1,4,5,6-tetrahydropyrimidine-4-carboxylic acid, is an extremely important small biomolecule belonging to the class of osmolytic/osmoprotective compounds. It stabilizes biomacromolecules such as DNA and proteins and protects them from denaturation by heat, dehydration, and UV radiation. The rapidly growing interest in this compound resulted in currently exclusive biotechnological production, while a chemical process along with enantioseparation as an alternative has not yet been established. An improved chemical synthesis of racemic ectoine starting from γ-butyrolactone in very good yield is described. Regioselective monoacetylation is achieved by the complexation of a copper(II)-ion with two molecules of 2,4-diamonobutyric acid in the key synthetic step. The racemic ectoine was synthesized with the aim of being successfully enantioseparated for the first time by high-performance liquid chromatography (HPLC) using a teicoplanin-based Chiral-T column in different solvent systems. The presence of (+)-ectoine was determined and quantified using an HPLC protocol on the Synergy Polar-RP column in fermentation broths inoculated with different strains of Streptomyces sp. bacteria isolated from the Adriatic Sea and grown on different NaCl concentrations.

Item Type:	Article
Uncontrolled Keywords:	ectoine; enantioseparation; chiral chromatography; osmoprotectant; marine bacteria; bioprospecting
Subjects:	NATURAL SCIENCES > Chemistry > Organic Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry Division of Physical Chemistry
Projects:	Project title Project leader Project code Project type Bioprospecting Jadranskog mora- Rozelinda Čož-Rakovac; Verica Dragović-Uzelac; Božidar Šantek; Stela Jokić; Igor Jerković; Sandra Kraljević Pavelić KK.01.1.1.01.0002 EK
Depositing User:	Lorena Palameta
Date Deposited:	29 Oct 2024 13:25
URI:	http://fulir.irb.hr/id/eprint/9220
DOI:	10.3390/app14188353

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