15205-57-9Relevant articles and documents
Synthesis and evaluation of a phosphonate analogue of the soluble guanylate cyclase activator YC-1
Martin, Nathaniel I.,Derbyshire, Emily R.,Marletta, Michael A.
, p. 4938 - 4941 (2007)
Soluble guanylate cyclase (sGC) is activated by the known benzylindazole derivative YC-1 [1-benzyl-3-(5′-hydroxymethyl-2′-furyl)-indazole]. YC-1 also acts synergistically with CO, activating sGC to a level comparable to that achieved upon binding of nitric oxide, the endogenous activator of sGC. We here describe the synthesis of a YC-1 phosphonate analogue with improved aqueous solubility as well as its effects on sGC.
Rapid and flexible synthesis of 1-deoxy-D-xylulose-5-phosphate, the substrate for 1-deoxy-D-xylulose-5-phosphate reductoisomerase.
Cox, Russell J,de Andres-Gomez, Ana,Godfrey, Christopher R A
, p. 3173 - 3177 (2003)
1-Deoxy-D-xylulose-5-phosphate (DXP) is a key intermediate in the non-mevalonate pathway to terpenoids in bacteria, and it is the substrate for the enzyme 1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXP-R). In order to study the mechanism of DXP-R, we required a flexible synthesis of the substrate which would allow the incorporation of isotopic labels, and the variation of the two stereocentres. Thus 1,4-dihydroxypent-2-yne was selectively reduced to give the E-olefin, and selective phosphorylation of the primary alcohol followed by oxidation of the secondary alcohol gave a substrate suitable for dihydroxylation. Dihydroxylation using stoichiometric OsO4 in the presence of chiral ligands gave protected DXP in high ee. Final hydrogenolysis gave DXP in quantitative yield and high purity. DXP-R was produced by rapid cloning of the dxr gene from Escherichia coli through controlled expression and ion exchange chromatography. The synthetic DXP was fully active in enzyme assays catalysed by recombinant DXP-R.
The synthesis and aqueous superoxide anion scavenging of water-dispersible lutein esters
Nadolski, Geoff,Cardounel, Arturo J.,Zweier, Jay L.,Lockwood, Samuel F.
, p. 775 - 781 (2006)
Xanthophyll carotenoids of the C40 series, which includes commercially important compounds such as lutein, zeaxanthin, and astaxanthin, have poor aqueous solubility in the native state. Hawaii Biotech, Inc. (HBI) and others have shown that the aqueous dispersibility of derivatized carotenoids can be increased by varying the chemical structure of the esterified moieties. In the current study, the published series of novel, highly water-dispersible C40 carotenoid derivatives has been extended to include (3R,3′R,6′R)- lutein (β,ε-carotene-3,3′-diol) derivatives. Two novel derivatives were synthesized by esterification with inorganic phosphate and succinic acid, respectively, and subsequently converted to the sodium salts. Red-orange, clear, aqueous suspensions were obtained after addition of these novel derivatives to USP-purified water. Aqueous dispersibility of the disuccinate sodium salt of lutein was 2.85 mg/mL; the diphosphate salt demonstrated a >10-fold increase in dispersibility at 29.27 mg/mL. As reported previously, these aqueous suspensions were obtained without the addition of heat, detergents, co-solvents, or other additives. The direct aqueous superoxide scavenging abilities of these novel derivatives were subsequently evaluated by electron paramagnetic resonance (EPR) spectroscopy in a well-characterized in vitro isolated human neutrophil assay. The novel derivatives were nearly identical aqueous-phase scavengers, demonstrating dose-dependent suppression of the superoxide anion signal (as detected by spin-trap adducts of DEPMPO) in the millimolar range. These lutein-based soft drugs will likely find utility in those commercial and clinical applications for which aqueous-phase singlet oxygen quenching and direct radical scavenging may be required.
Latent Ruthenium Benzylidene Phosphite Complexes for Visible-Light-Induced Olefin Metathesis
Baranov, Mark,Eivgi, Or,Lemcoff, N. Gabriel,Nechmad, Noy B.,Vaisman, Anna
, p. 2033 - 2038 (2020/02/11)
Herein we report two ruthenium benzylidene complexes with benzylphosphite ligands for olefin metathesis. Unlike the previously reported benzylidene phosphite complexes, the benzylphosphite complexes adopt a cis-dichloro configuration making them latent at ambient temperatures. Irradiation with visible light (420 nm and blue LED) prompts activation of the complexes and induces catalysis of olefin metathesis reactions. One of the complexes, cis-Ru-1, was found to be especially suitable for 3D printing of multilayered polydicyclopentadiene structures with excellent spatial resolutions. Additionally, complex cis-Ru-2 was designed with a chromatic orthogonal "kill switch" based on the 2-nitrobenzyl chemistry, allowing the destruction of the catalyst upon exposure to UV-C light.
INHIBITORS OF DXP SYNTHASE AND METHODS OF USE THEREOF
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Paragraph 0197; 0198, (2015/09/22)
Novel inhibitors of DXP synthase and methods of use thereof are disclosed.
