Synthesis of Enantiomerically Enriched Drug Precursors by Lactobacillus paracasei BD87E6 as a Biocatalyst
Küçük Resim Yok
Tarih
2018
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
Wiley-VCH Verlag
Erişim Hakkı
info:eu-repo/semantics/closedAccess
Özet
Global sales of single enantiomeric drug products are growing at an alarming rate every year. A total of 7 bacterial strains were screened for their ability to reduce acetophenones to its corresponding alcohol. Among these strains Lactobacillus paracasei BD87E6 was found to be the most successful biocatalyst to reduce the ketones to the corresponding alcohols. The reaction conditions were systematically optimized for the reducing agent Lactobacillus paracasei BD87E6, which showed high enantioselectivity and conversion for the bioreduction. The preparative scale asymmetric reduction of 3-methoxyacetophenone (1h) by Lactobacillus paracasei BD87E6 gave (R)-1-(3-methoxyphenyl)ethanol (2h) with 92% yield and 99% enantiomeric excess. Compound 2h could be used for the synthesis of (S)-rivastigmine which has a great potential for the treatment of Alzheimer's disease. This study demonstrates that Lactobacillus paracasei BD87E6 can be used as a biocatalyst to obtain chiral carbinol with excellent yield and selectivity. The whole cell catalyzed the reductions of ketone substrates on the preparative scale, demonstrating that Lactobacillus paracasei BD87E6 would be a valuable biocatalyst for the preparation of chiral aromatic alcohols of pharmaceutical interest. © 2018 Wiley-VHCA AG, Zurich, Switzerland
Açıklama
Anahtar Kelimeler
asymmetric synthesis, biocatalysis, chirality, drug precursor, Lactobacillus paracasei, 1 phenylethanol, acetophenone, acetophenone derivative, rivastigmine, methanol, Article, biocatalyst, catalysis, chemical reaction, chirality, enantioselectivity, high performance liquid chromatography, incubation time, Lactobacillus paracasei, nonhuman, pH, reaction analysis, reduction (chemistry), shear stress, substrate concentration, synthesis, temperature sensitivity, thin layer chromatography, whole cell, biocatalysis, chemical structure, chemistry, cytology, Lactobacillus paracasei, metabolism, oxidation reduction reaction, stereoisomerism, Biocatalysis, Lactobacillus paracasei, Methanol, Molecular Structure, Oxidation-Reduction, Rivastigmine, Stereoisomerism, asymmetric synthesis, biocatalysis, chirality, drug precursor, Lactobacillus paracasei, 1 phenylethanol, acetophenone, acetophenone derivative, rivastigmine, methanol, Article, biocatalyst, catalysis, chemical reaction, chirality, enantioselectivity, high performance liquid chromatography, incubation time, Lactobacillus paracasei, nonhuman, pH, reaction analysis, reduction (chemistry), shear stress, substrate concentration, synthesis, temperature sensitivity, thin layer chromatography, whole cell, biocatalysis, chemical structure, chemistry, cytology, Lactobacillus paracasei, metabolism, oxidation reduction reaction, stereoisomerism, Biocatalysis, Lactobacillus paracasei, Methanol, Molecular Structure, Oxidation-Reduction, Rivastigmine, Stereoisomerism
Kaynak
Chemistry and Biodiversity
WoS Q Değeri
Q3
Scopus Q Değeri
Q2
Cilt
15
Sayı
6
