JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
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2019
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IF 3.571
Cun-Duo Tang,Peng-Ju Ding,Hong-Ling Shi,Yuan-yuan Jia,Mao-zhi Zhou,Hui-lei Yu,Jian-He Xu,Lun-Guang Yao,Yun-Chao Kan
Phenylglyoxylic acid (PGA) are key building blocks and widely used to synthesize pharmaceutical intermediates or food additives. However, the existing synthetic methods for PGA generally involve toxic cyanide and complex processes. To explore an alternative method for PGA biosynthesis, we envisaged cascade biocatalysis for the one-pot synthesis of PGA from racemic mandelic acid. A novel mandelate racemase named ArMR showing higher expression level (216.9 U·mL–1 fermentation liquor) was cloned from Agrobacterium radiobacter and identified, and six recombinant Escherichia coli strains were engineered to coexpress three enzymes of mandelate racemase, d-mandelate dehydrogenase and l-lactate dehydrogenase, and transform racemic mandelic acid to PGA. Among them, the recombinant E. coli TCD 04, engineered to coexpress three enzymes of ArMR, LhDMDH, and LhLDH, can transform racemic mandelic acid (100 mM) to PGA with 98% conversion. Taken together, we provide a green approach for one-pot biosynthesis of PGA from racemic mandelic acid.
研究领域:
化学工程
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生物技术
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有机化学
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酶学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
ANALYTICA CHIMICA ACTA
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2022
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IF 6.911
Huanhuan Wang,Fangling Wu,Xinhua Dai,Xiang Fang,Chuan-Fan Ding
Because R/S-mandelic acids (MA) and their derivatives are critical starting materials or intermediates in the synthesis of chiral drugs, their chirality discrimination is important. In this study, R/S-MA and its derivatives, including R/S-2-phenylpropionic acid (2-PPA), R/S-methoxyphenylaceticacid (MPA), and R/S-2-hydroxy-4-phenylbutyric acid (HPBA), were accurate simultaneous mobility-discriminated by forming diastereomer complexes for the first time, which were obtained by simply mixing with cyclodextrins (α, β, γ-CD) and transition-metal ions (Mn 2+ , Fe 2+ , Co 2+ , Ni 2+ , Cu 2+ , and Zn 2+ ). The mass spectra revealed non-covalent diastereomer complexes formed by CD , enantiomers , and metal ions , and ion-mobility spectrometry (IMS) was performed for 109 pairs of complexes. Significant chiral discrimination was observed in the formed diastereomeric complexes, and their separation peak-to-peak resolution (R p−p ) for the enantiomers depended on the transition metal ion type. In most cases, the R p−p value gradually increases with CD size, with quaternary complexes having the largest R p−p value. The greatest chiral distinctions of 2-PPA, MA, MPA, and HPBA were obtained by the diastereomeric complex ions of [(2-PPA)(α) 2 +Zn 2+ -H] + , [(MA)(α) 2 +Zn 2+ -H] + , [(MPA) 2 (β)+Co 2+ -H] + , and [(HPBA)(α) 2 +Fe 2+ -H] + , with R p−p values of 1.35, 1.57, 1.70, and 0.71, respectively. Furthermore, the favorable conformation and collisional cross section (CCS) value of the different [CD + R/S-MA + Cu–H] + complexes were measured using chemical theoretical calculations to detail their intermolecular interaction , revealing that [α-CD + R/S-MA + Cu–H] + has two favored gas complexes, and the CCS calculated were consistent with the TIMS observed. In addition, R 2 > 0.99 was obtained for the relative quantification of the chiral enantiomers. Overall, the proposed method provides a promising strategy for distinguishing the enantiomers of MA and their derivatives, with the advantages of simplicity, speed, and accuracy, without the need for complex chemical derivatization or chromatographic separation.
研究领域:
分析化学
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药物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）