20312-36-1Relevant articles and documents
Novel camphane-based anti-tuberculosis agents with nanomolar activity
Stavrakov, Georgi,Valcheva, Violeta,Philipova, Irena,Doytchinova, Irini
, p. 372 - 379 (2013)
A series of new amidoalcohols and amidodiols were designed on the base of the camphor scaffold and evaluated for their in vitro activity against Mycobacterium tuberculosis H37Rv and MDR strain 43. Some of the new compounds show 25 times higher activity than the classical anti-TB drug ethambutol. Small structural changes in the side chain shift the activity from micromolar to nanomolar inhibitory concentrations. Quantitative structure-activity relationship (QSAR) model is derived to guide the further lead optimization. Two hydrogen bond donors and up to three rings in the molecules are optimal for nanomolar activity. The camphane-based amides present novel promising scaffolds for antimycobacterial agents.
Enantioselective biosynthesis of L-phenyllactic acid by whole cells of recombinant Escherichia coli
Zhu, Yibo,Wang, Ying,Xu, Jiayuzi,Chen, Jiahao,Wang, Limei,Qi, Bin
, (2017)
Background: L-Phenyllactic acid (L-PLA)—a valuable building block in the pharmaceutical and chemical industry—has recently emerged as an important monomer in the composition of the novel degradable biocompatible material of polyphenyllactic acid. However, both normally chemically synthesized and naturally occurring phenyllactic acid are racemic, and the product yields of reported L-PLA synthesis processes remain unsatisfactory. Methods: We developed a novel recombinant Escherichia coli strain, co-expressing L-lactate dehydrogenase (L-LDH) from Lactobacillus plantarum subsp. plantarum and glucose dehydrogenase (GDH) from Bacillus megaterium, to construct a recombinant oxidation/reduction cycle for whole-cell biotransformation of phenylpyruvic acid (PPA) into chiral L-PLA in an enantioselective and continuous manner. Results: During fed-batch bioconversion with intermittent PPA feeding, L-PLA yield reached 103.8 mM, with an excellent enantiomeric excess of 99.7%. The productivity of L-PLA was as high as 5.2 mM·h?1 per OD600 (optical density at 600 nm) of whole cells. These results demonstrate the efficient production of L-PLA by the one-pot biotransformation system. Therefore, this stereoselective biocatalytic process might be a promising alternative for L-PLA production.
Trikoveramides A-C, cyclic depsipeptides from the marine cyanobacterium Symploca hydnoides
Goh, Jun Xian,Katermeran, Nursheena Parveen,Phyo, Ma Yadanar,Tan, Lik Tong
, (2021/07/17)
Trikoveramides A – C, members of the kulolide superfamily of cyclic depsipeptides, were isolated from the marine cyanobacterium, Symploca hydnoides, collected from Bintan Island, Indonesia. Their planar structures were elucidated by a combination of NMR spectroscopy and HRMS spectral data. The absolute configurations of the amino acid and phenyllactic acid units were confirmed by Marfey's and chiral HPLC analyses, respectively, while the relative stereochemistry of the 3-hydroxy-2-methyl-7-octynoic acid (Hmoya) unit in trikoveramide A was elucidated by the application of the J-based configuration analysis and NOE correlations. The cytotoxic activity of the trikoveramides were evaluated against MOLT-4 human leukemia cells and gave IC50 values of 9.3 μM, 35.6 μM and 48.8 μM for trikoveramide B, trikoveramide C and trikoveramide A, respectively. In addition, trikoveramides A – C showed weak to moderate inhibition in the quorum sensing inhibitory assay based on the Pseudomonas aeruginosa lasB-gfp and rhlA-gfp bioreporter strains.
Total synthesis and absolute configuration determination of Ktedonoketone, a benzenoid metabolite from Thermophilic bacterium
Dandawate, Monica,Choudhury, Rahul,Rama Krishna, Gamidi,Srinivasa Reddy
supporting information, (2020/10/30)
The successful total synthesis of both enantiomers of ktedonoketone allowed us to decipher an unambiguous assignment of absolute configuration of the natural product. The concise synthesis highlights Wacker oxidation and aldol condensation as key steps. In addition to this, the current synthetic route is suitable to access a library of compounds on the similar skeleton as one can use readily available amino acids and Grignard reagents as variants.
