Search results for "absolute configuration"
showing 10 items of 121 documents
Helical supramolecular polymerization of C3-symmetric amides and retroamides: on the origin of cooperativity and handedness.
2016
The cooperative supramolecular polymerization of 1 and 2 yields P- or M-type helical aggregates depending on the absolute configuration (S or R) of the stereogenic centres attached to the side chains. The connectivity of the amide group does not affect the handedness of the helical aggregates, but determines a larger cooperativity for retroamides 1.
Isolation and identification of 4,6,8-trimethyl-7,9-undecadien-5-ol, a female-specific compound, in tergal gland secretion ofCryptocercus punctulatus…
1991
International audience; The secretion of the tergal glands of Cryptocercus punctulatus consists of a complex mixture of 27 compounds. Of this mixture, only one compound (compound B) is specific for females. By dissecting 200 tergal glands, 50 µg of pure compound B was collected by preparative GC; it was identified as (Z, E-4,6,8-trimethyl-7,9-undecadien-5-oI. Its functions as well as its absolute configuration still have to be determined.
Lasiolactols A and B Produced by the Grapevine Fungal Pathogen Lasiodiplodia mediterranea
2016
A strain of Lasiodiplodia mediterranea, a fungus associated with grapevine decline in Sicily, produced several metabolites in liquid medium. Two new dimeric c-lactols, lasiolactols A and B (1 and 2), were characterized as (2S*,3S*,4R*,5R*,20S*,30S*,40R*,50R*)-and (2R*,3S*,4R*,5R*,20R*,30S*,40R*,50R*)-(5-(4-hydroxymethyl-3,5-dimethyl-tetrahydrofuran- 2-yloxy)-2,4-dimethyl-tetrahydro-furan-3-yl]-methanols by IR, 1D-and 2D-NMR, and HR-ESI-MS. Other four metabolites were identified as botryosphaeriodiplodin, (5R)-5-hydroxylasiodiplodin, (-)-(1R, 2R)-jasmonic acid, and (-)-(3S, 4R, 5R)-4-hydroxymethyl-3,5-dimethyldihydro-2-furanone (3 - 6, resp.). The absolute configuration (R) at hydroxylated s…
Enantiospecific Brook Rearrangement of Tertiary Benzylic α-Hydroxysilanes
2018
The Brook rearrangement of simple, chiral tertiary benzylic -hydroxysilanes is presented. The rearrangement followed by proton trapping is enantiospecific and proceeds with inversion of the configuration at the carbon center. Importantly, the [1,2]-Brook rearrangement can be followed by trapping of methyl or allyl electrophiles even in the protic environment, although with minimal retention of chirality.
Synthesis and pharmacological characterization of beta2-adrenergic agonist enantiomers: zilpaterol.
2009
The beta-adrenergic agonist 1 (zilpaterol) is used as production enhancer in cattle. Binding experiments of separated enantiomers on recombinant human beta(2)-adrenergic and mu-opioid receptors and functional studies showed that the (-)-1 enantiomer accounts for essentially all the beta(2)-adrenergic agonist activity and that it exhibits less affinity toward the mu-opioid receptor than (+)-1, which is a mu-opioid receptor antagonist. X-ray crystallography revealed the absolute configuration of (-)-1 to be 6R,7R.
Modular P-Chirogenic Phosphine-Sulfide Ligands: Clear Evidence for Both Electronic Effect and P-Chirality Driving Enantioselectivity in Palladium-Cat…
2015
Using the ephedrine methodology, modular stereoselective syntheses of a new class of P-chirogenic phosphines bearing a sulfur-chelating arm (P*,S-hybrid ligand) are described. A first series of syntheses based on a Fries-like rearrangement of P-chirogenic phosphinite-boranes, which are prepared from 2-bromobenzyl or 2-bromophenethyl alcohol and are mediated by metal–halide exchange, have been performed. This rearrangement affords phosphine-boranes stereospecifically with an o-hydroxyalkylphenyl substituent. The latter residue is subsequently converted into a sulfur-containing group. In a second series, the stereoselective syntheses were achieved according to a new strategy involving a react…
Chemical constituents of the root wood of Erythrina sacleuxii and determination of the absolute configuration of suberectin
2020
Phytochemical investigation on the root wood of Erythrina sacleuxii (Leguminosae) led to the isolation of nine secondary metabolites (1-9). Compound 1 was isolated from the genus Erythrina for the first time. The pure compounds were identified on the basis of comprehensive spectroscopic and spectrometric analyses, while their absolute configurations were determined based on chiroptical measurements. Compounds 5 and 6 showed weak antifungal activity against Pyricularia oryzae with MIC values of 20 µg/mL.
 
 Bull. Chem. Soc. Ethiop. 2020, 34(1), 135-140.
 DOI: https://dx.doi.org/10.4314/bcse.v34i1.12
Two-carbon bridge substituted cocaines: enantioselective synthesis, attribution of the absolute configuration and biological activity of novel 6- and…
1999
In an effort to learn more about the general structure-activity relationships of cocaine with the aim to elucidate those structural features that might confer antagonistic properties to such analogues, we describe herein our synthetic efforts to prepare two-carbon bridge functionalized (methoxylated and hydroxylated) analogues. Our approach makes use of a modification of the classical Willstatter synthesis of cocaine: Mannich type cyclization of acetonedicarboxylic acid monomethyl ester with methylamine hydrochloride and 2-methoxysuccindialdehyde in a citrate buffer solution afforded the 6- and 7-substituted 2-carbomethoxy-3-tropinones 3a,b and 4a,b in approximate yields of 64%. Reduction o…
Gephyromycin, the first bridged angucyclinone, from Streptomyces griseus strain NTK 14
2005
The new, highly oxygenated angucyclinone gephyromycin was isolated from an extract of a Streptomyces griseus strain. Its unprecedented ether-bridged structure was elucidated by NMR methods and substantiated by single crystal X-ray analysis. The absolute configuration was evidenced by quantum chemical CD calculations. Gephyromycin exhibits glutaminergic activity towards neuronal cells. Furthermore, the known compounds fridamycin E and dehydrorabelomycin were identified.
Glutathione conjugation of trans-3,4-dihydroxy 1,2-epoxy l,2,3,4-tetrahydrobenzo[c]phenanthrene isomers by human glutathione transferases
1992
Each of the four stereoisomers of trans-3,4-dihydroxy 1,2-epoxy 1,2,3,4-tetrahydrobenzo[c]phenanthrene [(+)- and (-)-anti-BPhDE and (+)- and (-)-syn-BPhDE] has been incubated with the human glutathione transferase (GST) isoenzymes GST A1-1, GST M1-1 and GST P1-1, representing class alpha, mu and pi respectively, and glutathione (GSH). The conjugates formed were analyzed by HPLC and the results demonstrate that all GST isoenzymes catalyze the formation of GSH conjugates of all BPhDE isomers. However, a marked variation in catalytic efficiencies was observed (0.122-1.28/mM/s). These values are considerably lower than those previously estimated for the bay-region diol epoxides of benzo[a]pyren…