Bromination -nucleophilic attack by the alkene on bromine - forming a tertiary carbocation with bromonium ion character .-ion is attacked from the backside by bromide ion to form dibromocholesterol in the trans and diaxial configuration -practical purpose of purifying cholesterol. 6, 8100 (2015). 26, 11971211 (2016). Cooperative transcriptional activation of ATP-binding cassette sterol transporters ABCG5 and ABCG8 genes by nuclear receptors including Liver-X-Receptor. Moon, S. H. et al. USA 107, 1222812232 (2010). Pyripyropene A, an acyl-coenzyme A:cholesterol acyltransferase 2-selective inhibitor, attenuates hypercholesterolemia and atherosclerosis in murine models of hyperlipidemia. Deubiquitylase inhibition reveals liver X receptor-independent transcriptional regulation of the E3 ubiquitin ligase IDOL and lipoprotein uptake. Mol. Chem. Chang, C. C. Y. et al. Regulation of hepatic LDL receptors by mTORC1 and PCSK9 in mice. PDF 16. Electrophilic Aromatic Substitution - West Virginia University Lipogenic transcription factor ChREBP mediates fructose-induced metabolic adaptations to prevent hepatotoxicity. Walker, A. K. et al. Cooperative interaction between hepatocyte nuclear factor 4 and GATA transcription factors regulates ATP-binding cassette sterol transporters ABCG5 and ABCG8. Cell Metab. 33, 15031514 (2013). Zambrano, F., Fleischer, S. & Fleischer, B. Lipid composition of the Golgi apparatus of rat kidney and liver in comparison with other subcellular organelles. Med. Infante, R. E. & Radhakrishnan, A. Sever, N. et al. Biophys. Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations. Cardiol. Pharm. 13, 771782 (2006). N. Engl. Circ. Howe, V., Sharpe, L. J., Prabhu, A. V. & Brown, A. J. Annu. Schoebel, S. et al. J. Physiol. Chem. J. Biol. Mol. Lagace, T. A. et al. Lee, P. C. W., Sever, N. & DeBose-Boyd, R. A. 6, 13411347 (2000). Jakulj, L. et al. 53, 15981609 (2012). Li, P. S. et al. 27, 42484260 (2007). Cell Dev. Horton, J. D., Bashmakov, Y., Shimomura, I. The bromination of a double bond is an important and well-understood reaction. Nat. Res. Genet. 292, 1995919973 (2017). Wang, S. H., Gulshan, K., Brubaker, G., Hazen, S. L. & Smith, J. D. ABCA1 mediates unfolding of apolipoprotein AI N terminus on the cell surface before lipidation and release of nascent high-density lipoprotein. Cholesterol-regulated translocation of NPC1L1 to the cell surface facilitates free cholesterol uptake. Chem. Yang, C. D. et al. Rogers, M. A. et al. and JavaScript. The E3 ubiquitin ligase MARCH6 degrades squalene monooxygenase and affects 3-hydroxy-3-methyl-glutaryl coenzyme a reductase and the cholesterol synthesis pathway. Chem. Biochim. 14, 413419 (2007). Abrogating cholesterol esterification suppresses growth and metastasis of pancreatic cancer. J. Biol. 53, 20922101 (2012). COPII-coated vesicles exit from specialized regions of the ER membrane devoid ofbound ribosomes, known as ER exit sites, and deliver their content to the Golgi. Proc. (Autosomal recessive hypercholesterolaemia). Fitzgerald, M. L., Mujawar, Z. Sano, O. et al. J. Steroid Biochem. Tao, R. Y., Xiong, X. W., DePinho, R. A., Deng, C. X. Nat. Involvement of Akt in ER-to-Golgi transport of SCAP/SREBP: a link between a key cell proliferative pathway and membrane synthesis. 280, 3015030157 (2005). Bromine-Sudan Black: a general stain for lipids including free cholesterol Provided by the Springer Nature SharedIt content-sharing initiative, Journal of Animal Science and Biotechnology (2023), Nature Reviews Molecular Cell Biology (Nat Rev Mol Cell Biol) Mol. A protein that binds lipids to form lipoproteins, which then transport lipids and fat-soluble vitamins in circulation. This study uses parabiotic mice to show that PCSK9 secreted in plasma can degrade LDLR onthe surface of hepatocytes. USA 108, 1971919724 (2011). 263, 89298937 (1988). 5, 10921102 (2016). ACAT2 and ABCG5/G8 are both required for efficient cholesterol absorption in mice: evidence from thoracic lymph duct cannulation. & Edwards, P. A. ATP binding cassette transporter G1 (ABCG1) is an intracellular sterol transporter. organic chemistry - Electrophillic susbtitution of bromine on styrene 1, 179189 (2005). J. Clin. Cavelier, C., Lorenzi, I., Rohrer, L. & von Eckardstein, A. Lipid efflux by the ATP-binding cassette transporters ABCA1 and ABCG1. Article & Rudel, L. L. Identification of putative active site residues of ACAT enzymes. Open Access Chem. 284, 2885628864 (2009). Med. Open Access Cell Biol. & DeBose-Boyd, R. A. Sequential actions of the AAA-ATPase valosin-containing protein (VCP)/p97 and the proteasome 19S regulatory particle in sterol-accelerated, endoplasmic reticulum (ER)-associated degradation of 3-hydroxy-3-methylglutaryl-coenzyme A reductase. 51, 13541362 (2010). Chem. PubMed 284, 2248122490 (2009). Wang, J. et al. 294, 1583615849 (2019). Chem. Sci. This is a preview of subscription content, access via your institution. Article Biochem. Nuclear factor-B regulates the expression of multiple genes encoding liver transport proteins. PubMed To this solution is added dropwise a solution (c. 8 ml) of bromine in a acid containing sodium acetate via syringe. Together with reference 160, this work provides structural and biochemical evidence showing that PCSK9 directly binds to the EGF-A domain of LDLR. Proc. Zhang, X. J. et al. Wang, H. et al. Berge, K. E. et al. 285, 3349933509 (2010). J. In the present experiment, it is employed for the very practical purpose of purifying crude cholesterol through the process of bromination, crystallization, and then zinc dust debromination. Liver Physiol. Rev. 122, 16481660 (2018). A LIMA1 variant promotes low plasma LDL cholesterol and decreases intestinal cholesterol absorption.