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bromination of cholesterol mechanism

Li, B. L. et al. This step temporarily breaks the aromaticity in the ring. This study identifies an endocytic motif YVNxxF atthe C-terminal tail of NPC1L1. Costet, P., Luo, Y., Wang, N. & Tall, A. R. Sterol-dependent transactivation of the ABC1 promoter by the liver X receptor/retinoid X receptor. Quantitative gas-solid addition of bromine to cholesterol and the Rev. USA 107, 1222812232 (2010). Sci. 278, 4759447601 (2003). Cholesteryl ester accumulation induced by PTEN loss and PI3K/AKT activation underlies human prostate cancer aggressiveness. 278, 4827548282 (2003). Membrane topology of human NPC1L1, a key protein in enterohepatic cholesterol absorption. 286, 3593335942 (2011). & Chang, T. Y. (apo). Continuous transport of a small fraction of plasma membrane cholesterol to endoplasmic reticulum regulates total cellular cholesterol. Debromination of 473 and 468 was achieved by heating with sodium sulfite in aqueous solution to give 456 (1987ACSA(B)724).The 4,5-dibromo compound 476 was debrominated regioselectively furnishing the 4-bromo compound 473 (1987ACSA(B)724).The regioselectivity reflects that the 5-anion 475 according to H/D exchange rates is formed faster than the 4-anion 474 (Scheme 138). Biol. A classic laboratory experiment involving the bromination of cholesterol and subsequent zinc-mediated debromination back to cholesterol has been reworked for use in an upper-level organic. Chem. 62, 11171135 (2019). This study shows that hepatic ABCG5 and ABCG8 mediates cholesterol excretion into bile and that intestinal ABCG5 and ABCG8 contributes to cholesterol efflux via the non-hepatobiliary route. (NPC1). Based on the structures, the authors proposed that NPC1 receives cholesterol from NPC2 and inserts it into the lysosomal membrane. 309, 864872 (2003). C 160c, 250262 (2012). USA 104, 1509315098 (2007). and JavaScript. Drug Metab. Nguyen, T. M. et al. J. Physiol. Chem. Two genes that map to the STSL locus cause sitosterolemia: genomic structure and spectrum of mutations involving sterolin-1 and sterolin-2 encoded by ABCG5 and ABCG8 respectively. Chen, L. et al. Gong, X. et al. J.Lipid Res. Thromb. Together with reference 160, this work provides structural and biochemical evidence showing that PCSK9 directly binds to the EGF-A domain of LDLR. Song, B. L., Sever, N. & DeBose-Boyd, R. A. gp78, a membrane-anchored ubiquitin ligase, associates with Insig-1 and couples sterol-regulated ubiquitination to degradation of HMG CoA reductase. Bromination is a chemical reaction involving the reaction of a compound, and bromine results in bromine being added to the compound. Google Scholar. Chem. Science 292, 13941398 (2001). A class of naturally occurring organic compounds that are composed of two or more unitsof isoprene. Wang, N., Lan, D. B., Chen, W. 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Cell Metab. Eur. A role for oxysterol-binding protein-related protein 5 in endosomal cholesterol trafficking. 371, 20722082 (2014). J. Lipid Res. The GPI anchor is a unique mode of protein binding to the plasma membrane. Biophys. A steroid is a biologically active organic compound with four rings (AD) arranged in a specific molecular configuration. J. Biol. J. Lipid Res. Biochim. Mol. Quantitative gas-solid addition of bromine to cholesterol and the solid-solid esterification of cholesterol with oxalic acid. Du, X. et al. J. Biol. 278, 1556515570 (2003). Z., Jun, D. J., Seemann, J. In agreement with Schwenk and Werthessen, a single bromination and reconversion to cholesterol was usually sufficient to establish radiochemical purity of the isolated sterol. revised it. Circulation 125, 19051919 (2012). Chem. Yang, C. D. et al. The mixture was swirled for 5-10 minutes in the hood and sonicated in 5 minutes to allow the reaction to go completion. Atheroscler. The active site His-460 of human acyl-coenzyme A:cholesterol acyltransferase 1 resides in a hitherto undisclosed transmembrane domain. Chem. Cunningham, D. et al. The clathrin adaptor proteins ARH, Dab2, and numb play distinct roles in NiemannPick C1-Like 1 versus low density lipoprotein receptor-mediated cholesterol uptake. Lipids 1862, 647657 (2017). Biol. PLOS Genet. & Brown, A. J. Cholesterol-dependent degradation of squalene monooxygenase, a control point in cholesterol synthesis beyond HMG-CoA reductase. PubMed Central Vasc. An intracellular cholesterol-rich site composed of a mixture of individual and interconnected vesicles and tubules near the microtubule-organizing centre. Yang, J. The mevalonate pathway inmammals leads to the synthesis of sterols, isoprenoids, dolichol, haeme, ubiquinione and so forth. Infante, R. E. & Radhakrishnan, A. Open Access Natl Acad. 278, 1164211647 (2003). Biophys. Cell 176, 564580 (2019). Vrins, C. et al. 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Horie, T. et al. Alllylic bromination of 1-butene. Zhang, Y. Y. et al. Hong, C. et al. Padyana, A. K. et al. 292, 93829393 (2017). & Song, B. L. Intracellular cholesterol transport by sterol transfer proteins at membrane contact sites. USA 105, 1304513050 (2008). For the following bromination of 3-methylcyclopentene, . 57, 12861299 (2016). Lee, J. N., Gong, Y., Zhang, X. Y. J. Biol. & Namgaladze, D. AMPK activates LXR and ABCA1 expression in human macrophages. 374, 381388 (2000). & Ueda, K. ABCA1 dimermonomer interconversion during HDL generation revealed by single-molecule imaging. Jeon, H. & Blacklow, S. C. Structure and physiologic function of the low-density lipoprotein receptor. Trends Biochem. 119, 827838 (2016). (LDLs). ABCA1, ABCG1, and ABCG4 are distributed to distinct membrane meso-domains and disturb detergent-resistant domains on the plasma membrane. 36, 285294 (2016). Joyce, C. W. et al. Genet. Science 325, 100104 (2009). Lopez, D., Abisambra Socarras, J. F., Bedi, M. & Ness, G. C. Activation of the hepatic LDL receptor promoter by thyroid hormone. Natl Acad. Small heterodimer partner and fibroblast growth factor 19 inhibit expression of NPC1L1 in mouse intestine and cholesterol absorption. Chem. Jo, Y. et al. 292, 30163028 (2017). Chem. A MARCH6 and IDOL E3 ubiquitin ligase circuit uncouples cholesterol synthesis from lipoprotein uptake in hepatocytes. Lipidol. Conserved role of SIRT1 orthologs in fasting-dependent inhibition of the lipid/cholesterol regulator SREBP. Oram, J. F. & Heinecke, J. W. ATP-binding cassette transporter A1: a cell cholesterol exporter that protects against cardiovascular disease. Kemmerer, M., Wittig, I., Richter, F., Brune, B. Why does acetate ion not attack the intermediate bromonium ion to give the 5-acetoxy-6-bromo compound in the bromination of cholesterol?

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