Catalytic mechanism of a retinoid isomerase essential for vertebrate vision

Kiser, Philip D; Zhang, Jianye; Badiee, Mohsen; Li, Qingjiang; Shi, Wuxian; Sui, Xuewu; Golczak, Marcin; Tochtrop, Gregory P; Palczewski, Krzysztof

doi:10.1038/nchembio.1799

Title: Catalytic mechanism of a retinoid isomerase essential for vertebrate vision

Journal Article · Fri Oct 02 00:00:00 EDT 2015 · Nat. Chem. Biol.

DOI:https://doi.org/10.1038/nchembio.1799· OSTI ID:1197044

Kiser, Philip D; Zhang, Jianye; Badiee, Mohsen; Li, Qingjiang; Shi, Wuxian; Sui, Xuewu; Golczak, Marcin; Tochtrop, Gregory P; Palczewski, Krzysztof ^[1]

Case Western

Cite

Export

Save

Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States). Advanced Photon Source (APS)

Sponsoring Organization:: NSFOTHER U.S. GOVERNMENTNIH

OSTI ID:: 1197044

Journal Information:: Nat. Chem. Biol., Vol. 11, Issue 04, 2015

Country of Publication:: United States

Language:: ENGLISH

References (49)

Electrostatics of nanosystems: Application to microtubules and the ribosome Baker, N. A.; Sept, D.; Joseph, S. Proceedings of the National Academy of Sciences, Vol. 98, Issue 18, p. 10037-10041 https://doi.org/10.1073/pnas.181342398	journal	August 2001
Crystal Structure of Pentalenene Synthase: Mechanistic Insights on Terpenoid Cyclization Reactions in Biology Lesburg, C. A. Science, Vol. 277, Issue 5333 https://doi.org/10.1126/science.277.5333.1820	journal	September 1997
Overview of the CCP 4 suite and current developments Winn, Martyn D.; Ballard, Charles C.; Cowtan, Kevin D. Acta Crystallographica Section D Biological Crystallography, Vol. 67, Issue 4 https://doi.org/10.1107/S0907444910045749	journal	March 2011
Identification of the Key Residues Determining the Product Specificity of Isomerohydrolase Takahashi, Yusuke; Moiseyev, Gennadiy; Nikolaeva, Olga Biochemistry, Vol. 51, Issue 20 https://doi.org/10.1021/bi300144n	journal	May 2012
A New Generation of Crystallographic Validation Tools for the Protein Data Bank Read, Randy J.; Adams, Paul D.; Arendall, W. Bryan Structure, Vol. 19, Issue 10 https://doi.org/10.1016/j.str.2011.08.006	journal	October 2011
The Resolution of Important Pharmaceutical Building Blocks by Palladium-Catalyzed Aerobic Oxidation of Secondary Alcohols Caspi, Daniel D.; Ebner, David C.; Bagdanoff, Jeffrey T. Advanced Synthesis & Catalysis, Vol. 346, Issue 23 https://doi.org/10.1002/adsc.200303188	journal	February 2004
RPE65 Is an Iron(II)-dependent Isomerohydrolase in the Retinoid Visual Cycle Moiseyev, Gennadiy; Takahashi, Yusuke; Chen, Ying Journal of Biological Chemistry, Vol. 281, Issue 5 https://doi.org/10.1074/jbc.M508903200	journal	November 2005
Structural Insights into Maize Viviparous14, a Key Enzyme in the Biosynthesis of the Phytohormone Abscisic Acid Messing, Simon A. J.; Gabelli, Sandra B.; Echeverria, Ignacia The Plant Cell, Vol. 22, Issue 9 https://doi.org/10.1105/tpc.110.074815	journal	September 2010
A conjugate addition–radical cyclisation approach to sesquiterpene-phenol natural products Crombie, Barry S.; Smith, Colin; Varnavas, Christalla Z. Journal of the Chemical Society, Perkin Transactions 1, Issue 2 https://doi.org/10.1039/b005617k	journal	January 2001
Retinyl Esters Are the Substrate for Isomerohydrolase ^† Moiseyev, Gennadiy; Crouch, Rosalie K.; Goletz, Patrice Biochemistry, Vol. 42, Issue 7 https://doi.org/10.1021/bi026911y	journal	February 2003
Cation-pi Interactions in Chemistry and Biology: A New View of Benzene, Phe, Tyr, and Trp Dougherty, D. A. Science, Vol. 271, Issue 5246 https://doi.org/10.1126/science.271.5246.163	journal	January 1996
Molecular Basis of Visual Excitation Wald, G. Science, Vol. 162, Issue 3850 https://doi.org/10.1126/science.162.3850.230	journal	October 1968
A helical lid converts a sulfotransferase to a dehydratase Pakhomova, Svetlana; Kobayashi, Mime; Buck, Jochen Nature Structural Biology, Vol. 8, Issue 5, p. 447-451 https://doi.org/10.1038/87617	journal	May 2001
Membranes as the energy source in the endergonic transformation of vitamin A to 11-cis-retinol Deigner, P.; Law, W.; Canada, F. Science, Vol. 244, Issue 4907 https://doi.org/10.1126/science.2727688	journal	May 1989
RPE65, Visual Cycle Retinol Isomerase, Is Not Inherently 11- cis -specific : SUPPORT FOR A CARBOCATION MECHANISM OF RETINOL ISOMERIZATION Redmond, T. Michael; Poliakov, Eugenia; Kuo, Stephanie Journal of Biological Chemistry, Vol. 285, Issue 3 https://doi.org/10.1074/jbc.M109.027458	journal	November 2009
Positively charged retinoids are potent and selective inhibitors of the trans-cis isomerization in the retinoid (visual) cycle Golczak, M.; Kuksa, V.; Maeda, T. Proceedings of the National Academy of Sciences, Vol. 102, Issue 23 https://doi.org/10.1073/pnas.0503318102	journal	May 2005
Crystal structure of native RPE65, the retinoid isomerase of the visual cycle Kiser, P. D.; Golczak, M.; Lodowski, D. T. Proceedings of the National Academy of Sciences, Vol. 106, Issue 41 https://doi.org/10.1073/pnas.0906600106	journal	October 2009
XDS Kabsch, Wolfgang Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 2 https://doi.org/10.1107/S0907444909047337	journal	January 2010
Mutation of key residues of RPE65 abolishes its enzymatic role as isomerohydrolase in the visual cycle Redmond, T. M.; Poliakov, E.; Yu, S. Proceedings of the National Academy of Sciences, Vol. 102, Issue 38 https://doi.org/10.1073/pnas.0504167102	journal	September 2005
Stereochemical inversion at C-15 accompanies the enzymic isomerization of all-trans- to 11-cis-retinoids Law, Wing C.; Rando, Robert R. Biochemistry, Vol. 27, Issue 11 https://doi.org/10.1021/bi00411a037	journal	May 1988
Carbonium ion of all-trans-retinyl acetate. Spectroscopic detection and identification of absorbing species. Effect of environment on spectral properties Blatz, Paul E.; Pippert, David L. Journal of the American Chemical Society, Vol. 90, Issue 5 https://doi.org/10.1021/ja01007a033	journal	February 1968
Isomerization of all - trans -Retinol to cis -Retinols in Bovine Retinal Pigment Epithelial Cells: Dependence on the Specificity of Retinoid-Binding Proteins ^† McBee, Joshua K.; Kuksa, Vladimir; Alvarez, Rosana Biochemistry, Vol. 39, Issue 37 https://doi.org/10.1021/bi001061c	journal	September 2000
Chapter 2: Hydrolysis and Formation of Esters of Organic Acids Kirby, A. J. Comprehensive Chemical Kinetics. Ester Formation and Hydrolysis and Related Reactions https://doi.org/10.1016/S0069-8040(08)70344-3	book	January 1972
The Structure of a Retinal-Forming Carotenoid Oxygenase Kloer, D. P. Science, Vol. 308, Issue 5719 https://doi.org/10.1126/science.1108965	journal	April 2005
Molecular surface generation using a variable-radius solvent probe Bhat, Sathesh; Purisima, Enrico O. Proteins: Structure, Function, and Bioinformatics, Vol. 62, Issue 1 https://doi.org/10.1002/prot.20682	journal	November 2005
Analysis of Carotenoid Isomerase Activity in a Prototypical Carotenoid Cleavage Enzyme, Apocarotenoid Oxygenase (ACO) Sui, Xuewu; Kiser, Philip D.; Che, Tao Journal of Biological Chemistry, Vol. 289, Issue 18 https://doi.org/10.1074/jbc.M114.552836	journal	March 2014
Vitamin A Metabolism in Rod and Cone Visual Cycles Saari, John C. Annual Review of Nutrition, Vol. 32, Issue 1 https://doi.org/10.1146/annurev-nutr-071811-150748	journal	August 2012
Crystal Structure of Rhodopsin: A G Protein-Coupled Receptor Palczewski, K. Science, Vol. 289, Issue 5480 https://doi.org/10.1126/science.289.5480.739	journal	August 2000
Surprises and pitfalls arising from (pseudo)symmetry Zwart, Peter H.; Grosse-Kunstleve, Ralf W.; Lebedev, Andrey A. Acta Crystallographica Section D Biological Crystallography, Vol. 64, Issue 1 https://doi.org/10.1107/S090744490705531X	journal	December 2007
MolProbity : all-atom structure validation for macromolecular crystallography Chen, Vincent B.; Arendall, W. Bryan; Headd, Jeffrey J. Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 1 https://doi.org/10.1107/S0907444909042073	journal	December 2009
Features and development of Coot Emsley, P.; Lohkamp, B.; Scott, W. G. Acta Crystallographica Section D Biological Crystallography, Vol. 66, Issue 4 https://doi.org/10.1107/S0907444910007493	journal	March 2010
REFMAC 5 for the refinement of macromolecular crystal structures Murshudov, Garib N.; Skubák, Pavol; Lebedev, Andrey A. Acta Crystallographica Section D Biological Crystallography, Vol. 67, Issue 4 https://doi.org/10.1107/S0907444911001314	journal	March 2011
On the treatment of negative intensity observations French, S.; Wilson, K. Acta Crystallographica Section A, Vol. 34, Issue 4 https://doi.org/10.1107/S0567739478001114	journal	July 1978
Diseases Caused by Defects in the Visual Cycle: Retinoids as Potential Therapeutic Agents Travis, Gabriel H.; Golczak, Marcin; Moise, Alexander R. Annual Review of Pharmacology and Toxicology, Vol. 47, Issue 1 https://doi.org/10.1146/annurev.pharmtox.47.120505.105225	journal	February 2007
Aromatic Residues in the Substrate Cleft of RPE65 Protein Govern Retinol Isomerization and Modulate Its Progression Chander, Preethi; Gentleman, Susan; Poliakov, Eugenia Journal of Biological Chemistry, Vol. 287, Issue 36 https://doi.org/10.1074/jbc.M112.364596	journal	June 2012
Fluorescence spectrum of the retinylic cation Blatz, Paul E.; Pippert, David L. Chemical Communications (London), Issue 4 https://doi.org/10.1039/c19680000176	journal	January 1968
Chemistry of the Retinoid (Visual) Cycle Kiser, Philip D.; Golczak, Marcin; Palczewski, Krzysztof Chemical Reviews, Vol. 114, Issue 1 https://doi.org/10.1021/cr400107q	journal	July 2013
Structure and Function of a Squalene Cyclase Wendt, K. U. Science, Vol. 277, Issue 5333 https://doi.org/10.1126/science.277.5333.1811	journal	September 1997
Preferential Release of 11- cis- retinol from Retinal Pigment Epithelial Cells in the Presence of Cellular Retinaldehyde-binding Protein Stecher, Hartmut; Gelb, Michael H.; Saari, John C. Journal of Biological Chemistry, Vol. 274, Issue 13 https://doi.org/10.1074/jbc.274.13.8577	journal	March 1999
Importance of Membrane Structural Integrity for RPE65 Retinoid Isomerization Activity Golczak, Marcin; Kiser, Philip D.; Lodowski, David T. Journal of Biological Chemistry, Vol. 285, Issue 13 https://doi.org/10.1074/jbc.M109.063941	journal	January 2010
Mutations in RPE65 cause Leber's congenital amaurosis Marlhens, Françoise; Bareil, Corinne; Griffoin, Jean-Michel Nature Genetics, Vol. 17, Issue 2 https://doi.org/10.1038/ng1097-139	journal	October 1997
Phase 1, Dose-Ranging Study of Emixustat Hydrochloride (Acu-4429), a Novel Visual Cycle Modulator, in Healthy Volunteers Kubota, Ryo; Al-Fayoumi, Suliman; Mallikaarjun, Suresh Retina, Vol. 34, Issue 3 https://doi.org/10.1097/01.iae.0000434565.80060.f8	journal	January 2014
Structure of RPE65 isomerase in a lipidic matrix reveals roles for phospholipids and iron in catalysis Kiser, P. D.; Farquhar, E. R.; Shi, W. Proceedings of the National Academy of Sciences, Vol. 109, Issue 41 https://doi.org/10.1073/pnas.1212025109	journal	September 2012
Synthesis of (±)-thaps-7(15)-ene and (±)-thaps-6-enes Srikrishna, Adusumilli; Krishnan, Kathiresan J. Chem. Soc., Perkin Trans. 1, Issue 6 https://doi.org/10.1039/P19930000667	journal	January 1993
The Resolution of Important Pharmaceutical Building Blocks by Palladium-Catalyzed Aerobic Oxidation of Secondary Alcohols. Caspi, Daniel D.; Ebner, David C.; Bagdanoff, Jeffrey T. ChemInform, Vol. 35, Issue 31 https://doi.org/10.1002/chin.200431025	journal	August 2004
AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading Trott, Oleg; Olson, Arthur J. Journal of Computational Chemistry https://doi.org/10.1002/jcc.21334	journal	January 2009
Stereoisomeric Specificity of the Retinoid Cycle in the Vertebrate Retina Jang, Geeng-Fu; McBee, Joshua K.; Alekseev, Andrei M. Journal of Biological Chemistry, Vol. 275, Issue 36 https://doi.org/10.1074/jbc.m004488200	journal	September 2000
Statistical quality indicators for electron-density maps Tickle, Ian J. Acta Crystallographica Section D Biological Crystallography, Vol. 68, Issue 4 https://doi.org/10.1107/s0907444911035918	journal	March 2012
BIOCHEMISTRY: Creating Isoprenoid Diversity Sacchettini, J. C. Science, Vol. 277, Issue 5333 https://doi.org/10.1126/science.277.5333.1788	journal	September 1997

Cited By (12)

Few Layer 2D Pnictogens (P & Sb) Catalyze the Alkylation of Soft Nucleophiles with Esters Lioret, Vincet; Rivero-Crespo, Miguel Angel; Vidal-Moya, Jose Alejandro Nanoscience https://doi.org/10.26434/chemrxiv.7123184.v1	preprint	September 2018
Structural biology of 11-cis-retinaldehyde production in the classical visual cycle Daruwalla, Anahita; Choi, Elliot H.; Palczewski, Krzysztof Biochemical Journal, Vol. 475, Issue 20 https://doi.org/10.1042/bcj20180193	journal	October 2018
Molecular Basis for Vitamin A Uptake and Storage in Vertebrates Chelstowska, Sylwia; Widjaja-Adhi, Made; Silvaroli, Josie Nutrients, Vol. 8, Issue 11 https://doi.org/10.3390/nu8110676	journal	October 2016
The selective estrogen receptor modulator raloxifene mitigates the effect of all- trans -retinal toxicity in photoreceptor degeneration Getter, Tamar; Suh, Susie; Hoang, Thanh Journal of Biological Chemistry, Vol. 294, Issue 24 https://doi.org/10.1074/jbc.ra119.008697	journal	May 2019
Few layer 2D pnictogens catalyze the alkylation of soft nucleophiles with esters Lloret, Vicent; Rivero-Crespo, Miguel Ángel; Vidal-Moya, José Alejandro Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-018-08063-3	journal	January 2019
Retinoid isomerase inhibitors impair but do not block mammalian cone photoreceptor function Kiser, Philip D.; Zhang, Jianye; Sharma, Aditya Journal of General Physiology, Vol. 150, Issue 4 https://doi.org/10.1085/jgp.201711815	journal	March 2018
Few Layer 2D Pnictogens (P & Sb) Catalyze the Alkylation of Soft Nucleophiles with Esters Lloret, Vicent; Rivero-Crespo, Miguel Angel; Vidal-Moya, Jose Alejandro Nanoscience https://doi.org/10.26434/chemrxiv.7123184	preprint	September 2018
RPE65 takes on another role in the vertebrate retina Redmond, T. Michael Proceedings of the National Academy of Sciences, Vol. 114, Issue 41 https://doi.org/10.1073/pnas.1715064114	journal	October 2017
Molecular pharmacodynamics of emixustat in protection against retinal degeneration Zhang, Jianye; Kiser, Philip D.; Badiee, Mohsen Journal of Clinical Investigation, Vol. 125, Issue 7 https://doi.org/10.1172/jci80950	journal	June 2015
Preparation and characterization of metal-substituted carotenoid cleavage oxygenases Sui, Xuewu; Farquhar, Erik R.; Hill, Hannah E. JBIC Journal of Biological Inorganic Chemistry, Vol. 23, Issue 6 https://doi.org/10.1007/s00775-018-1586-0	journal	June 2018
Targeted Multifunctional Lipid ECO Plasmid DNA Nanoparticles as Efficient Non-viral Gene Therapy for Leber’s Congenital Amaurosis Sun, Da; Sahu, Bhubanananda; Gao, Songqi Molecular Therapy - Nucleic Acids, Vol. 7 https://doi.org/10.1016/j.omtn.2017.02.005	journal	June 2017
Towards Treatment of Stargardt Disease: Workshop Organized and Sponsored by the Foundation Fighting Blindness Sears, Avery E.; Bernstein, Paul S.; Cideciyan, Artur V. Translational Vision Science & Technology, Vol. 6, Issue 5 https://doi.org/10.1167/tvst.6.5.6	journal	September 2017

Similar Records

Catalytic mechanism of a retinoid isomerase essential for vertebrate vision

Journal Article · Mon Apr 20 00:00:00 EDT 2015 · Nature Chemical Biology · OSTI ID:1197044

Kiser, Philip D.; Zhang, Jianye; Badiee, Mohsen; +6 more

Crystal structure of native RPE65, the retinoid isomerase of the visual cycle

Journal Article · Tue Dec 01 00:00:00 EST 2009 · Proc. Natl. Acad. Sci. USA · OSTI ID:1197044

Kiser, Philip D; Golczak, Marcin; Lodowski, David T; +2 more

Assay of the retinoid isomerase system of the eye

Journal Article · Mon Jan 01 00:00:00 EST 1990 · Methods in Enzymology; (USA) · OSTI ID:1197044

Bernstein, P S; Rando, R R

Title: Catalytic mechanism of a retinoid isomerase essential for vertebrate vision

Citation Formats

References (49)

Cited By (12)

Similar Records

Related Subjects