Different transformations of chiral epoxy esters 1 afford two different amino gamma-butyrolactones 2 and 6, and amino gamma-butenolides 8, by different nucleophilic opening-closing processes. [reaction: see text]
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/ol0255918 | DOI Listing |
Chembiochem
December 2023
State Key Laboratory of Bioreactor Engineering, Shanghai Collaborative Innovation Center for Biomanufacturing, School of Biotechnology, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China.
(R)-β-piperonyl-γ-butyrolactones are key building blocks for the synthesis of podophyllotoxin, which have demonstrated remarkable potential in cancer treatment. Baeyer-Villiger monooxygenases (BVMOs)-mediated asymmetric oxidation is a green approach to produce chiral lactones. While several BVMOs were able to oxidize the corresponding cyclobutanone, most BVMOs gave the (S) enantiomer while Cyclohexanone monooxygenase (CHMO) from Brevibacterium sp.
View Article and Find Full Text PDFCurr Res Food Sci
October 2022
State Key Laboratory of Applied Microbiology Southern China, Guangdong Provincial Key Laboratory of Microbial Safety and Health, Key Laboratory of Agricultural Microbiomics and Precision Application, Ministry of Agriculture and Rural Affairs, Guangdong Institute of Microbiology, Guangdong Academy of Sciences, Guangzhou, 510070, China.
A novel bis-γ-butyrolactone grifolamine A (), the first γ-butyrolactone dimer from nature, together with three known γ-butyrolactones (-), was isolated from the byproduct from polysaccharides preparation process. The structure and stereochemistry of grifolamine A were elucidated by extensive spectroscopic analysis combined with quantum chemical calculation. The biosynthetic origin of compound , as well as - was proposed.
View Article and Find Full Text PDFFront Pharmacol
October 2022
Department of Pharmacognosy, Faculty of Pharmacy, Helwan University, Helwan, Egypt.
Prostate cancer (PCa) ranks as one of the most commonly diagnosed malignancies worldwide. Toxicity, lack of clinical efficacy, and development of resistance phenotypes are the main challenges in the control of prostate malignancies. Notably, castration-resistance prostate cancer (CRPCa) is a highly aggressive and metastatic phenotype of the disease with a poor prognosis and very limited therapeutic options.
View Article and Find Full Text PDFFront Cell Infect Microbiol
January 2022
Department of Cardiology, The First Affiliated Hospital of Nanjing Medical University, Nanjing, China.
Hookworm is one type of soil-transmitted helminth, which could exert an anti-inflammatory effect in human or animal host, which provides a beneficial possibility for the discovery of inflammatory-related disease interventions. The identification of hookworm-derived anti-inflammatory molecules is urgently needed for future translational research. The emergence of metabolomics has become a powerful approach to comprehensively characterize metabolic alterations in recent times.
View Article and Find Full Text PDFACS Catal
April 2021
Institute for Advanced Chemistry of Catalonia, Department of Biological Chemistry, IQAC-CSIC, Jordi Girona 18-24, Barcelona 08034, Spain.
Three enzymatic routes toward γ-hydroxy-α-amino acids by tandem aldol addition-transamination one-pot two-step reactions are reported. The approaches feature an enantioselective aldol addition of pyruvate to various nonaromatic aldehydes catalyzed by --hydroxybenzylidene pyruvate hydratase-aldolase (HBPA) from . This affords chiral 4-hydroxy-2-oxo acids, which were subsequently enantioselectively aminated using -selective transaminases.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!