While B(C(6)F(5))(3) forms the adducts (CH(2))(4)CO(2)B(C(6)F(5))(3)1 and (CHMeCO(2))(2)B(C(6)F(5))(3)7 with δ-valerolactone and lactide, the frustrated Lewis pairs derived from B(C(6)F(5))(3) and phosphine or N-bases react with lactone to effect ring opening affording zwitterionic species of the form L(CH(2))(4)CO(2)B(C(6)F(5))(3) (L = tBu(3)P 2, Cy(3)P 3, C(5)H(3)Me(3)N 4, PhNMe(2) 5, C(5)H(6)Me(4)NH 6) while reaction with rac-lactide results in ring contraction to give salts [LH][OCCHMeCO(2)(CMe)OB(C(6)F(5))(3)] (L = tBu(3)P 8, Cy(3)P 9, C(5)H(3)Me(2)N 10, C(5)H(6)Me(4)NH 11). The mechanistic implications of these reactions are discussed.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/c1dt10449g | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
A Novel Screening System to Characterize and Engineer Quorum Quenching Lactonases.
Biotechnol Bioeng
January 2025
Department of Biochemistry, Molecular Biology and Biophysics, University of Minnesota, St. Paul, Minnesota, USA.
N-acyl l-homoserine lactones are signaling molecules used by numerous bacteria in quorum sensing. Some bacteria encode lactonases, which can inactivate these signals. Lactonases were reported to inhibit quorum sensing-dependent phenotypes, including virulence and biofilm.
View Article and Find Full Text PDFA Novel Rhodamine-Based Fluorescent Sensor for Detection of Cu.
J Fluoresc
January 2025
School of Chemistry & Environmental Engineering, Jilin Provincial International Joint Research Center of Photo-Functional Materials and Chemistry, Changchun University of Science and Technology, Changchun, 130022, China.
In this work, a new fluorescent sensor for detecting Cu was developed based on the Rhodamine derivative. It displayed strong fluorescence enhancement upon the addition of Cu, and other common metal ions do not significantly affect the optical properties of the sensor. This optical signal change caused solely by Cu is due to the opening of the lactone amide spiro ring structure, resulting in fluorescence emission.
View Article and Find Full Text PDFRevealing the Monooxygenase Mechanism for Selective Ring Cleavage of Anthraquinone by BTG13 through Multiscale Simulations.
Chembiochem
January 2025
Renmin University of China, Chemistry, No.59 Zhongguangcun Street, Haidian District, 100872, Beijing, CHINA.
BTG13, a non-heme iron-dependent enzyme with a distinctive coordination environment of four histidines and a carboxylated lysine, has been found to catalyze the cleavage of the C4a-C10 bond in anthraquinone. Contrary to typical dioxygenase mechanisms, our quantum mechanical/molecular mechanical (QM/MM) calculations reveal that BTG13 functions more like a monooxygenase. It selectively inserts an oxygen atom into the C10-C4a bond, creating a lactone species that subsequently hydrolyzes, leading to the formation of a ring-opened product.
View Article and Find Full Text PDFSynthesis and exploration of anticancer potential of spirocyclic 1,2,3-triazoline and aziridine derivatives of natural eudesmanolide isoalantolactone.
Bioorg Chem
January 2025
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Lavrentyev Avenue 9, Novosibirsk 630090, Russia. Electronic address:
Eudesmane-type sesquiterpene lactone isoalantolactone 1 is of great interest due to its availability, biological activity and synthetic application. Respective series of original spirocyclic (11S,5') (1,2,3-triazoline-eudesma-4,15-enolides) and (11S)-aziridine-eudesma-4,15-enolides were efficiently synthesized via a chemoselective 1,3-dipolar cycloaddition reaction of organic azides to the exocyclic double bond of the lactone ring of isoalantolactone or 13E-(aryl)isoalantolactones by heating in DMF or toluene. The thermal reactions of isoalantolactone with benzyl azide, 2-azidoethanol, or n-butyl azide in 2-methoxyethanol afforded 13-(alkyamino)isoalantolactones formed as a mixture of (Z) and (E)-isomers.
View Article and Find Full Text PDFArtemisinin Stimulates Neuronal Cell Viability and Possess a Neuroprotective Effect In Vitro.
Molecules
January 2025
Institute of Physiologically Active Compounds, Federal Research Center of Problems of Chemical Physics and Medicinal Chemistry, Russian Academy of Sciences, 142432 Chernogolovka, Russia.
Artemisinin is a sesquiterpene lactone derived from the plant L., renowned for its antimalarial activity. Based on this compound, various derivatives and analogues have been obtained that exhibit diverse biological activities, including clinically approved drugs.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!