604-35-3Relevant academic research and scientific papers
Orientation of fluorinated cholesterol in lipid bilayers analyzed by 19F tensor calculation and solid-state NMR
Matsumori, Nobuaki,Kasai, Yusuke,Oishi, Tohru,Murata, Michio,Nomura, Kaoru
, p. 4757 - 4766 (2008)
6-F-cholesterol was reported to exhibit biological and interfacial properties similar to unmodified cholesterol. We have also found that 6-F-cholesterol mimicked the cholesterol activity observed in the systems of amphotericin B and lipid rafts. However, to use 6-F-cholesterol as a molecular probe to explore molecular recognition in membranes, it is indispensable to have detailed knowledge of the dynamic and orientation properties of the molecule in membrane environments. In this paper, we present the molecular orientation of 6-F-cholesterol (30 mol %) in dimyristoylphosphatidylcholine (DMPC) bilayers revealed by combined use of 19F chemical shift anisotropy (CSA), 2H NMR, and C-F rotational echo double resonance (REDOR) experiments. The axis of rotation of 6-F-cholesterol was shown to be in a similar direction to that of cholesterol in DMPC bilayers, which is almost parallel to the long axis of the molecular frame. The molecular order parameter of 6-F-cholesterol was determined to be ca. 0.85, which is within the range of reported values of cholesterol. These findings suggest that the dynamic properties of 6-F-cholesterol in DMPC are quite similar to those of unmodified cholesterol; therefore, the introduction of a fluorine atom at C6 has virtually no effect on cholesterol dynamics in membranes. In addition, this study demonstrates the practical utility of theoretical calculations for determining the 19F CSA principal axes, which would be extremely difficult to obtain experimentally. The combined use of quantum calculations and solid-state 19F NMR will make it possible to apply the orientation information of 19F CSA tensors to membrane systems.
Self-assembly of novel cholesterol derivative based on hydrogen bond
Yu, Yun-Long,Du, Hai-Yan,Zhang, Jun-Hua
, p. 107 - 112 (2011)
In this paper, a novel cholesterol derivative was found that it can form regular arrangement with millimeter size when we investigated the synthesis of new cholesterol monomer. The quite interesting thing is that the arrangement can form on common glass sheet after the sample is heating above its melting point and then cooling to room temperature. This is different from most reported regular arrangements formed in solutions. According to the single crystal results of the sample, we believe that the arrangement formed in solid state can be attributed to hydrogen bonding formed between molecular and Van der Waals force among molecular.
Characterization of heparin and severe acute respiratory syndrome-related coronavirus 2 (SARS-CoV-2) spike glycoprotein binding interactions
Dordick, Jonathan S.,Fu, Li,Fuster, Mark M.,Grant, Oliver C.,Jin, Weihua,Kim, So Young,Linhardt, Robert J.,Montgomery, David W.,Sood, Amika,Woods, Robert J.,Zhang, Fuming
, (2020)
Severe acute respiratory syndrome-related coronavirus 2 (SARS-CoV-2) has resulted in a pandemic and continues to spread around the globe at an unprecedented rate. To date, no effective therapeutic is available to fight its associated disease, COVID-19. Our discovery of a novel insertion of glycosaminoglycan (GAG)-binding motif at S1/S2 proteolytic cleavage site (681–686 (PRRARS)) and two other GAG-binding-like motifs within SARS-CoV-2 spike glycoprotein (SGP) led us to hypothesize that host cell surface GAGs may interact SARS-CoV-2 SGPs to facilitate host cell entry. Using a surface plasmon resonance direct binding assay, we found that both monomeric and trimeric SARS-CoV-2 SGP bind more tightly to immobilized heparin (KD = 40 pM and 73 pM, respectively) than the SARS-CoV and MERS-CoV SGPs (500 nM and 1 nM, respectively). In competitive binding studies, the IC50 of heparin, tri-sulfated non-anticoagulant heparan sulfate, and non-anticoagulant low molecular weight heparin against SARS-CoV-2 SGP binding to immobilized heparin were 0.056 μM, 0.12 μM, and 26.4 μM, respectively. Finally, unbiased computational ligand docking indicates that heparan sulfate interacts with the GAG-binding motif at the S1/S2 site on each monomer interface in the trimeric SARS-CoV-2 SGP, and at another site (453–459 (YRLFRKS)) when the receptor-binding domain is in an open conformation. The current study serves a foundation to further investigate biological roles of GAGs in SARS-CoV-2 pathogenesis. Furthermore, our findings may provide additional basis for further heparin-based interventions for COVID-19 patients exhibiting thrombotic complications.
3β-Acetoxy cholest-5-ene crystals: Catalytic synthesis, structural elucidation, contribution of intermolecular interactions and density functional theory calculations
Ahmad, Shabbir,Ahmed, Musheer,Alam, Mohammad Jane,Amer, Bushra,Mashrai, Ashraf
, (2020)
In this work, we present the synthesis of 3β-acetoxy cholest-5-ene using zinc triflate Zn(OTf)2 as a catalyst. The synthesized molecule has been characterized by single crystal XRD, spectroscopic techniques and density functional theory (DFT) calculations. The compound crystallizes in the monoclinic space group P21 with cell dimensions, a = 16.585(2) ?, b = 9.5175(12) ?, c = 17.656(2) ?, α = 90.00, β = 106.369(4), γ = 90.00. The systematic analysis of intermolecular interactions in crystal structure was accomplished by Hirshfeld surface analysis and fingerprint plot. Molecules are linked by a combination of C?H, C?C, H?H and O?H contacts, which have clear signatures in the fingerprint plots. The theoretical DFT/B3LYP calculations have been attempted to obtain the optimized geometry, IR/NMR spectra, natural bond orbitals, frontier molecular orbitals and various structure based molecular properties. We compared the conformations of the compound in solid state and in solution by calculation of dihedral angles and coupling constant values.
Site-selective and metal-free aliphatic C-H oxidation enabled synthesis of [5,24,25-d3]-(25s)-δ7-dafachronic acid
Liu, Weilong,Li, Xiangke,Chen, Jie,Li, Tiemei,Dong, Mengqiu,Lei, Xiaoguang
, p. 5345 - 5349 (2015)
Steroid hormones play significant roles in both worms and mammalians. (25S)-Δ7-Dafachronic acid (Δ7-DA, 1) is a member of the dafachronic acid hormonal series that regulates both development and lifespan of C. elegans. Despite its importance, effective tools for the illumination of its mode of action are lacking. Herein, we report an efficient synthesis of trideuterated Δ7-DA, [5,24,25-D3]-(25S)-Δ7-dafachronic acid ([D3]-Δ7-DA, 2), as a useful chemical tool for subsequent biological studies. Key steps for this bioinspired synthesis approach include site-selective aliphatic C-H oxidation mediated by methyl(trifluoromethyl)dioxirane (TFDO), and the iridium/phosphine-oxazoline-catalyzed late-stage asymmetric deuterium reduction. Bio is best! [5,24,25-D3]-(25S)-Δ7-Dafachronic acid, an isotope-labeled steroid hormone has been synthesized in 14 steps from cholesterol inspired by biosynthesis. Key steps include a site-selective and metal-free aliphatic C-H oxidation and a late-stage catalytic asymmetric deuteration (see scheme). [5,24,25-D3]-(25S)-Δ7-Dafachronic acid will be severed as an effective chemical tool for the illumination of novel molecular mechanisms of longevity.
IMIDAZOLE MEDIATED ACYLATION OF CHOLESTEROL IN FUNCTIONAL VESICLES: A SIMPLE ANALOGUE OF LECITHIN:CHOLESTEROL ACYLTRANSFERASE
Moss, Robert A.,Bhattacharya, Santanu,Okumura, Yukihisa
, p. 4905 - 4908 (1989)
Imidazole-functionalized surfactants transfer acetyl groups from p-nitrophenyl acetate to cholesterol in vesicular coaggregates.
Method for synthesizing cholesterol by taking BA as raw material
-
, (2021/08/14)
The invention discloses a method for synthesizing cholesterol by taking BA as a raw material. A plant source raw material 21-hydroxy-20-methylpregna-4-en-3-one, also known as Shuangjiangchun or BA is taken as a raw material, and the cholesterol is synthesized by the steps of oxidation, Wittig reaction, acetylation, reduction, selective hydrogenation reduction and the like. The raw materials for synthesizing cholesterol are plant sources, the price is low, the safety is high, the risk of pathogenic bacteria and virus infection is avoided, and the synthesis method is easy to operate, high in yield, few in side reaction, environmentally friendly, good in economical efficiency and convenient for industrial production; and the invention solves the safety problem of the existing cholesterol product and the problems of high cost, environmental unfriendliness and unsuitability for large-scale industrial production in the synthesis technology.
Novel industrial method for preparing vitamin D3 by taking stigmasterol as raw material
-
, (2021/05/05)
The invention provides a novel industrial method for preparing vitamin D3 by taking stigmasterol as a raw material. The method comprises the following steps: sequentially carrying out hydroxyl acetylation, side chain oxidation, side chain isopentane reduction and hydrogenation on stigmasterol to obtain cholesterol acetate, and then sequentially carrying out oxidation, hydrazone formation, hydrazone removal, hydrolysis, illumination and the like to obtain the vitamin D3. The invention provides a novel method for preparing vitamin D3 from stigmasterol, and the method has the advantages of mild reaction conditions and high yield, and is suitable for industrial production.
KMnO4-catalyzed chemoselective deprotection of acetate and controllable deacetylation-oxidation in one pot
Gurawa, Aakanksha,Kumar, Manoj,Rao, Dodla S.,Kashyap, Sudhir
supporting information, p. 16702 - 16707 (2020/10/27)
A novel and efficient protocol for chemoselective deacetylation under ambient conditions was developed using catalytic KMnO4. The stoichiometric use of KMnO4 highlighted the dual role of a heterogeneous oxidant enabling direct access to aromatic aldehydes in one-pot sequential deacetylation-oxidation. The reaction employed an alternative solvent system and allowed the clean transformation of benzyl acetate to sensitive aldehyde in a single step while preventing over-oxidation to acids. Use of inexpensive and readily accessible KMnO4 as an environmentally benign reagent and the ease of the reaction operation were particularly attractive, and enabled the controlled oxidation and facile cleavage of acetate in a preceding step. This journal is
HALOGENATED CHOLESTEROL ANALOGUES AND METHODS OF MAKING AND USING SAME
-
Paragraph 0088-0091, (2020/05/12)
Provided herein are halogenated cholesterol analogues, including methods of making and using the same. Also provided are methods of making radiolabeled cholesterol analogues including admixing an epoxide with a fluorine-18 source under conditions to form a radiofluorinated cholesterol analogue.
