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

Q1 Mathematics Applied Sciences Pub Date : 2024-09-17 DOI:10.3390/app14188353

Marcela Šišić, Mladenka Jurin, Ana Šimatović, Dušica Vujaklija, Andreja Jakas, Marin Roje

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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.

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应用生物技术和手性技术方法生产外辛烯对映体

天然外氨酸（(+)-(4S)-2-甲基-1,4,5,6-四氢嘧啶-4-羧酸）是一种极其重要的小型生物大分子，属于渗透/渗透保护化合物。它能稳定 DNA 和蛋白质等生物大分子，保护它们不受热、脱水和紫外线辐射的影响而变性。人们对这种化合物的兴趣与日俱增，因此目前只能采用生物技术进行生产，而化学工艺和对映体分离作为一种替代方法尚未确立。本文介绍了一种以γ-丁内酯为起始原料的外消旋辛内酯的改进化学合成方法，收率非常高。在关键合成步骤中，通过铜（II）离子与两分子 2,4-二氨基丁酸的络合，实现了区域选择性单乙酰化。合成外消旋外藤碱的目的是在不同溶剂系统中使用基于茶碱的手性-T色谱柱，通过高效液相色谱法（HPLC）首次成功地进行对映体分离。在接种了从亚得里亚海分离的不同链霉菌菌株并在不同氯化钠浓度下生长的发酵液中，使用 Synergy Polar-RP 柱上的 HPLC 方案测定并量化了 (+)-ectoine 的存在。

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来源期刊

Applied Sciences Mathematics-Applied Mathematics

CiteScore

6.40

自引率

0.00%

发文量

审稿时长

11 weeks

期刊介绍： APPS is an international journal. APPS covers a wide spectrum of pure and applied mathematics in science and technology, promoting especially papers presented at Carpato-Balkan meetings. The Editorial Board of APPS takes a very active role in selecting and refereeing papers, ensuring the best quality of contemporary mathematics and its applications. APPS is abstracted in Zentralblatt für Mathematik. The APPS journal uses Double blind peer review.