Thioester synthesis by a designed nickel enzyme models prebiotic energy conversion

Manesis, Anastasia C.; Yerbulekova, Alina; Shearer, Jason; Shafaat, Hannah S.

doi:10.1073/pnas.2123022119

Title: Thioester synthesis by a designed nickel enzyme models prebiotic energy conversion

Journal Article · Mon Jul 18 00:00:00 EDT 2022 · Proceedings of the National Academy of Sciences of the United States of America

DOI:https://doi.org/10.1073/pnas.2123022119· OSTI ID:1876508

^[1];

^[1]; Shearer, Jason ^[2];

^[3]

The Ohio State Biochemistry Program, The Ohio State University, Columbus, OH 43210
Department of Chemistry, Trinity University, San Antonio, TX 78212
The Ohio State Biochemistry Program, The Ohio State University, Columbus, OH 43210, Department of Chemistry and Biochemistry, The Ohio State University, Columbus, OH 43210

The formation of carbon–carbon bonds from prebiotic precursors such as carbon dioxide represents the foundation of all primordial life processes. In extant organisms, this reaction is carried out by the carbon monoxide dehydrogenase (CODH)/acetyl coenzyme A synthase (ACS) enzyme, which performs the cornerstone reaction in the ancient Wood–Ljungdahl metabolic pathway to synthesize the key biological metabolite, acetyl-CoA. Despite its significance, a fundamental understanding of this transformation is lacking, hampering efforts to harness analogous chemistry. To address these knowledge gaps, we have designed an artificial metalloenzyme within the azurin protein scaffold as a structural, functional, and mechanistic model of ACS. We demonstrate the intermediacy of the Ni ^I species and requirement for ordered substrate binding in the bioorganometallic carbon–carbon bond-forming reaction from the one-carbon ACS substrates. The electronic and geometric structures of the nickel-acetyl intermediate have been characterized using time-resolved optical, electron paramagnetic resonance, and X-ray absorption spectroscopy in conjunction with quantum chemical calculations. Moreover, we demonstrate that the nickel-acetyl species is chemically competent for selective acyl transfer upon thiol addition to biosynthesize an activated thioester. Drawing an analogy to the native enzyme, a mechanism for thioester generation by this ACS model has been proposed. The fundamental insight into the enzymatic process provided by this rudimentary ACS model has implications for the evolution of primitive ACS-like proteins. Ultimately, these findings offer strategies for development of highly active catalysts for sustainable generation of liquid fuels from one-carbon substrates, with potential for broad applications across diverse fields ranging from energy storage to environmental remediation.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0018020

OSTI ID:: 1876508

Journal Information:: Proceedings of the National Academy of Sciences of the United States of America, Journal Name: Proceedings of the National Academy of Sciences of the United States of America Vol. 119 Journal Issue: 30; ISSN 0027-8424

Publisher:: Proceedings of the National Academy of SciencesCopyright Statement

Country of Publication:: United States

Language:: English

References (66)

The Copper(II) Adduct of the Unstructured Region of the Amyloidogenic Fragment Derived from the Human Prion Protein is Redox-Active at Physiological pH Shearer, Jason; Soh, Pamela Inorganic Chemistry, Vol. 46, Issue 3 https://doi.org/10.1021/ic061236s	journal	January 2007
Nucleophilicities of amino acids and peptides Brotzel, Frank; Mayr, Herbert Organic & Biomolecular Chemistry, Vol. 5, Issue 23 https://doi.org/10.1039/b713778h	journal	January 2007
Activated Acetic Acid by Carbon Fixation on (Fe,Ni)S Under Primordial Conditions Huber, C. Science, Vol. 276, Issue 5310 https://doi.org/10.1126/science.276.5310.245	journal	April 1997
Synthesis and Reactivity of Two-Coordinate Ni(I) Alkyl and Aryl Complexes Laskowski, Carl A.; Bungum, Donald J.; Baldwin, Steven M. Journal of the American Chemical Society, Vol. 135, Issue 49 https://doi.org/10.1021/ja4095236	journal	November 2013
Cysteinate Protonation and Water Hydrogen Bonding at the Active-Site of a Nickel Superoxide Dismutase Metallopeptide-Based Mimic: Implications for the Mechanism of Superoxide Reduction Shearer, Jason; Peck, Kristy L.; Schmitt, Jennifer C. Journal of the American Chemical Society, Vol. 136, Issue 45 https://doi.org/10.1021/ja5079514	journal	November 2014
Construction and characterization of an azurin analog for the purple copper site in cytochrome c oxidase. Hay, M.; Richards, J. H.; Lu, Y. Proceedings of the National Academy of Sciences, Vol. 93, Issue 1 https://doi.org/10.1073/pnas.93.1.461	journal	January 1996
Rapid Kinetic Studies of Acetyl-CoA Synthesis: Evidence Supporting the Catalytic Intermediacy of a Paramagnetic NiFeC Species in the Autotrophic Wood−Ljungdahl Pathway Seravalli, Javier; Kumar, Manoj; Ragsdale, Stephen W. Biochemistry, Vol. 41, Issue 6 https://doi.org/10.1021/bi011687i	journal	January 2002
Synthetic analogs for evaluating the influence of N–H⋯S hydrogen bonds on the formation of thioester in acetyl coenzyme a synthase Ariyananda, Piyal W. G.; Kieber-Emmons, Matthew T.; Yap, Glenn P. A. Dalton Transactions, Issue 22 https://doi.org/10.1039/b901192g	journal	January 2009
Controlled potential enzymology of methyl transfer reactions involved in acetyl-CoA synthesis by CO dehydrogenase and the corrinoid/iron-sulfur protein from Clostridium thermoaceticum. Lu, W. P.; Harder, S. R.; Ragsdale, S. W. Journal of Biological Chemistry, Vol. 265, Issue 6 https://doi.org/10.1016/S0021-9258(19)39743-1	journal	February 1990
Why copper is preferred over iron for oxygen activation and reduction in haem-copper oxidases Bhagi-Damodaran, Ambika; Michael, Matthew A.; Zhu, Qianhong Nature Chemistry, Vol. 9, Issue 3 https://doi.org/10.1038/nchem.2643	journal	November 2016
A Possible Primordial Peptide Cycle Huber, C. Science, Vol. 301, Issue 5635 https://doi.org/10.1126/science.1086501	journal	August 2003
Photoredox Nickel-Catalyzed C–S Cross-Coupling: Mechanism, Kinetics, and Generalization Qin, Yangzhong; Sun, Rui; Gianoulis, Nikolas P. Journal of the American Chemical Society, Vol. 143, Issue 4 https://doi.org/10.1021/jacs.0c11937	journal	January 2021
X-ray Absorption Spectroscopy Reveals an Organometallic Ni–C Bond in the CO-Treated Form of Acetyl-CoA Synthase Can, Mehmet; Giles, Logan J.; Ragsdale, Stephen W. Biochemistry, Vol. 56, Issue 9 https://doi.org/10.1021/acs.biochem.6b00983	journal	February 2017
Control of Thiolate Nucleophilicity and Specificity in Zinc Metalloproteins by Hydrogen Bonding: Lessons from Model Compound Studies Smith, Jennifer N.; Shirin, Zahida; Carrano, Carl J. Journal of the American Chemical Society, Vol. 125, Issue 4 https://doi.org/10.1021/ja029418i	journal	December 2002
Electrochemical, Spectroscopic, and Density Functional Theory Characterization of Redox Activity in Nickel-Substituted Azurin: A Model for Acetyl-CoA Synthase Manesis, Anastasia C.; Shafaat, Hannah S. Inorganic Chemistry, Vol. 54, Issue 16 https://doi.org/10.1021/acs.inorgchem.5b01103	journal	August 2015
Multielectron Chemistry within a Model Nickel Metalloprotein: Mechanistic Implications for Acetyl-CoA Synthase Manesis, Anastasia C.; O’Connor, Matthew J.; Schneider, Camille R. Journal of the American Chemical Society, Vol. 139, Issue 30 https://doi.org/10.1021/jacs.7b03892	journal	July 2017
X-ray Spectroscopy of Nitrile Hydratase at pH 7 and 9 Scarrow, Robert C.; Brennan, Bridget A.; Cummings, John G. Biochemistry, Vol. 35, Issue 31 https://doi.org/10.1021/bi960164l	journal	January 1996
The Relative Rates of Thiol–Thioester Exchange and Hydrolysis for Alkyl and Aryl Thioalkanoates in Water Bracher, Paul J.; Snyder, Phillip W.; Bohall, Brooks R. Origins of Life and Evolution of Biospheres, Vol. 41, Issue 5 https://doi.org/10.1007/s11084-011-9243-4	journal	July 2011
Stopped-Flow Kinetics of Methyl Group Transfer between the Corrinoid-Iron-Sulfur Protein and Acetyl-Coenzyme A Synthase from Clostridium t hermoaceticum Tan, Xiang Shi; Sewell, Christopher; Lindahl, Paul A. Journal of the American Chemical Society, Vol. 124, Issue 22 https://doi.org/10.1021/ja016676r	journal	May 2002
Computational Studies on the A Cluster of Acetyl-Coenzyme A Synthase: Geometric and Electronic Properties of the NiFeC Species and Mechanistic Implications Schenker, Ralph P.; Brunold, Thomas C. Journal of the American Chemical Society, Vol. 125, Issue 46 https://doi.org/10.1021/ja037893q	journal	October 2003
Methylation of Carbon Monoxide Dehydrogenase from Clostridium thermoaceticum and Mechanism of Acetyl Coenzyme A Synthesis Barondeau, David P.; Lindahl, Paul A. Journal of the American Chemical Society, Vol. 119, Issue 17 https://doi.org/10.1021/ja963597k	journal	April 1997
Negative-Stain Electron Microscopy Reveals Dramatic Structural Rearrangements in Ni-Fe-S-Dependent Carbon Monoxide Dehydrogenase/Acetyl-CoA Synthase Cohen, Steven E.; Brignole, Edward J.; Wittenborn, Elizabeth C. Structure, Vol. 29, Issue 1 https://doi.org/10.1016/j.str.2020.08.011	journal	January 2021
Nickel-Mediated Formation of Thio Esters from Bound Methyl, Thiols, and Carbon Monoxide: A Possible Reaction Pathway of Acetyl-Coenzyme A Synthase Activity in Nickel-Containing Carbon Monoxide Dehydrogenases Tucci, Gregory C.; Holm, R. H. Journal of the American Chemical Society, Vol. 117, Issue 24 https://doi.org/10.1021/ja00129a011	journal	June 1995
Pulse-Chase Studies of the Synthesis of Acetyl-CoA by Carbon Monoxide Dehydrogenase/Acetyl-CoA Synthase Seravalli, Javier; Ragsdale, Stephen W. Journal of Biological Chemistry, Vol. 283, Issue 13 https://doi.org/10.1074/jbc.M709470200	journal	March 2008
EPR and Infrared Spectroscopic Evidence That a Kinetically Competent Paramagnetic Intermediate is Formed When Acetyl-Coenzyme A Synthase Reacts with CO George, Simon J.; Seravalli, Javier; Ragsdale, Stephen W. Journal of the American Chemical Society, Vol. 127, Issue 39 https://doi.org/10.1021/ja0528329	journal	September 2005
Thiolate Bridging and Metal Exchange in Adducts of a Zinc Finger Model and Pt ^II Complexes: Biomimetic Studies of Protein/Pt/DNA Interactions Almaraz, Elky; de Paula, Queite A.; Liu, Qin Journal of the American Chemical Society, Vol. 130, Issue 19 https://doi.org/10.1021/ja711254q	journal	April 2008
From Widely Accepted Concepts in Coordination Chemistry to Inverted Ligand Fields Hoffmann, Roald; Alvarez, Santiago; Mealli, Carlo Chemical Reviews, Vol. 116, Issue 14 https://doi.org/10.1021/acs.chemrev.6b00251	journal	June 2016
First-Row Transition-Metal Chloride Complexes of the Wide Bite-Angle Diphosphine ^iPr DPDBFphos and Reactivity Studies of Monovalent Nickel Marlier, Elodie E.; Tereniak, Stephen J.; Ding, Keying Inorganic Chemistry, Vol. 50, Issue 19 https://doi.org/10.1021/ic200589e	journal	October 2011
A Designed Metalloenzyme Achieving the Catalytic Rate of a Native Enzyme Yu, Yang; Cui, Chang; Liu, Xiaohong Journal of the American Chemical Society, Vol. 137, Issue 36 https://doi.org/10.1021/jacs.5b07119	journal	September 2015
The physiology and habitat of the last universal common ancestor Weiss, Madeline C.; Sousa, Filipa L.; Mrnjavac, Natalia Nature Microbiology, Vol. 1, Issue 9 https://doi.org/10.1038/nmicrobiol.2016.116	journal	July 2016
Structural insights into methyltransfer reactions of a corrinoid iron-sulfur protein involved in acetyl-CoA synthesis Svetlitchnaia, T.; Svetlitchnyi, V.; Meyer, O. Proceedings of the National Academy of Sciences, Vol. 103, Issue 39, p. 14331-14336 https://doi.org/10.1073/pnas.0601420103	journal	September 2006
The Conversion of Nickel-Bound CO into an Acetyl Thioester: Organometallic Chemistry Relevant to the Acetyl Coenzyme A Synthase Active Site Horn, Bettina; Limberg, Christian; Herwig, Christian Angewandte Chemie International Edition, Vol. 50, Issue 52 https://doi.org/10.1002/anie.201105281	journal	November 2011
Nitrogenase reactivity with P-cluster variants Hu, Y.; Corbett, M. C.; Fay, A. W. Proceedings of the National Academy of Sciences, Vol. 102, Issue 39 https://doi.org/10.1073/pnas.0506967102	journal	September 2005
Scrutinizing “Ligand Bands” via Polarized Single-Crystal X-ray Absorption Spectra of Copper(I) and Copper(II) Bis-2,2′-bipyridine Species DiMucci, Ida M.; MacMillan, Samantha N.; Walroth, Richard C. Inorganic Chemistry, Vol. 59, Issue 18 https://doi.org/10.1021/acs.inorgchem.0c01800	journal	September 2020
Transmethylation of a four-coordinate nickel( i ) monocarbonyl species with methyl iodide Yoo, Changho; Oh, Seohee; Kim, Jin Chem. Sci., Vol. 5, Issue 10 https://doi.org/10.1039/C4SC01089B	journal	January 2014
Acetyl-coenzyme A synthase: the case for a Nip0-based mechanism of catalysis Lindahl, Paul A. JBIC Journal of Biological Inorganic Chemistry, Vol. 9, Issue 5 https://doi.org/10.1007/s00775-004-0564-x	journal	June 2004
¹³ C Electron Nuclear Double Resonance Spectroscopy Shows Acetyl-CoA Synthase Binds Two Substrate CO in Multiple Binding Modes and Reveals the Importance of a CO-Binding “Alcove” James, Christopher D.; Wiley, Seth; Ragsdale, Stephen W. Journal of the American Chemical Society, Vol. 142, Issue 36 https://doi.org/10.1021/jacs.0c05950	journal	August 2020
Photoredox Mediated Nickel Catalyzed Cross-Coupling of Thiols With Aryl and Heteroaryl Iodides via Thiyl Radicals Oderinde, Martins S.; Frenette, Mathieu; Robbins, Daniel W. Journal of the American Chemical Society, Vol. 138, Issue 6 https://doi.org/10.1021/jacs.5b11244	journal	February 2016
Crystallographic Characterization of the Carbonylated A-Cluster in Carbon Monoxide Dehydrogenase/Acetyl-CoA Synthase Cohen, Steven E.; Can, Mehmet; Wittenborn, Elizabeth C. ACS Catalysis, Vol. 10, Issue 17 https://doi.org/10.1021/acscatal.0c03033	journal	August 2020
Organometallic chemistry of sulfur/phosphorus donor ligand complexes of nickel(II) and nickel(0) Hsiao, Yui May; Chojnacki, Stephen S.; Hinton, Pamela Organometallics, Vol. 12, Issue 3 https://doi.org/10.1021/om00027a041	journal	March 1993
Strong metal-to-ligand charge transfer bands observed in Ni K - and L -edge XANES of planar Ni complexes Hatsui, T.; Takata, Y.; Kosugi, N. Journal of Synchrotron Radiation, Vol. 6, Issue 3 https://doi.org/10.1107/S0909049599001338	journal	May 1999
Nitrosomonas europaea cytochrome P460 is a direct link between nitrification and nitrous oxide emission Caranto, Jonathan D.; Vilbert, Avery C.; Lancaster, Kyle M. Proceedings of the National Academy of Sciences, Vol. 113, Issue 51 https://doi.org/10.1073/pnas.1611051113	journal	November 2016
Reactivity of polynuclear zinc-thiolate sites Ohanessian, Gilles; Picot, Delphine; Frison, Gilles International Journal of Quantum Chemistry, Vol. 111, Issue 6 https://doi.org/10.1002/qua.22866	journal	August 2010
Structure, Function, and Mechanism of the Nickel Metalloenzymes, CO Dehydrogenase, and Acetyl-CoA Synthase Can, Mehmet; Armstrong, Fraser A.; Ragsdale, Stephen W. Chemical Reviews, Vol. 114, Issue 8 https://doi.org/10.1021/cr400461p	journal	February 2014
Kinetic characterization of the [3'-32P]coenzyme A/acetyl coenzyme A exchange catalyzed by a three-subunit form of the carbon monoxide dehydrogenase/acetyl-CoA synthase from Clostridium thermoaceticum Ramer, Shawn E.; Raybuck, Scott A.; Orme-Johnson, William H. Biochemistry, Vol. 28, Issue 11 https://doi.org/10.1021/bi00437a025	journal	May 1989
From protein engineering to artificial enzymes – biological and biomimetic approaches towards sustainable hydrogen production Esmieu, C.; Raleiras, P.; Berggren, G. Sustainable Energy & Fuels, Vol. 2, Issue 4 https://doi.org/10.1039/C7SE00582B	journal	January 2018
Infrared and EPR Spectroscopic Characterization of a Ni(I) Species Formed by Photolysis of a Catalytically Competent Ni(I)-CO Intermediate in the Acetyl-CoA Synthase Reaction Bender, Güneş; Stich, Troy A.; Yan, Lifen Biochemistry, Vol. 49, Issue 35 https://doi.org/10.1021/bi1010128	journal	August 2010
Electronic Structure Control of the Nucleophilicity of Transition Metal−Thiolate Complexes: An Experimental and Theoretical Study Fox, Derek C.; Fiedler, Adam T.; Halfen, Heather L. Journal of the American Chemical Society, Vol. 126, Issue 24 https://doi.org/10.1021/ja039419q	journal	May 2004
Redox-Dependent Acetyl Transfer Partial Reaction of the Acetyl-CoA Decarbonylase/Synthase Complex: Kinetics and Mechanism Bhaskar, B.; DeMoll, Edward; Grahame, David A. Biochemistry, Vol. 37, Issue 41 https://doi.org/10.1021/bi9812423	journal	September 1998
Binuclear Complexes Containing a Methylnickel Moiety: Relevance to Organonickel Intermediates in Acetyl Coenzyme A Synthase Catalysis Dougherty, William G.; Rangan, Krishnan; O’Hagan, Molly J. Journal of the American Chemical Society, Vol. 130, Issue 41 https://doi.org/10.1021/ja803795k	journal	September 2008
Mechanistic Study on C–C Bond Formation of a Nickel(I) Monocarbonyl Species with Alkyl Iodides: Experimental and Computational Investigations Yoo, Changho; Ajitha, Manjaly J.; Jung, Yousung Organometallics, Vol. 34, Issue 17 https://doi.org/10.1021/acs.organomet.5b00548	journal	August 2015
Ligand Field Inversion as a Mechanism to Gate Bioorganometallic Reactivity: Investigating a Biochemical Model of Acetyl CoA Synthase Using Spectroscopy and Computation Kisgeropoulos, Effie C.; Manesis, Anastasia C.; Shafaat, Hannah S. Journal of the American Chemical Society, Vol. 143, Issue 2 https://doi.org/10.1021/jacs.0c10135	journal	January 2021
Reductive activation of the coenzyme A/acetyl-CoA isotopic exchange reaction catalyzed by carbon monoxide dehydrogenase from Clostridium thermoaceticum and its inhibition by nitrous oxide and carbon monoxide Lu, W. P.; Ragsdale, S. W. Journal of Biological Chemistry, Vol. 266, Issue 6 https://doi.org/10.1016/S0021-9258(19)67831-2	journal	February 1991
Environment of Copper in Pseudomonas aeruginosa Azurin Probed by Binding of Exogenous Ligands to Met121X (X = Gly, Ala, Val, Leu, or Asp) Mutants Bonander, Nicklas; Karlsson, B. Göran; Vänngård, Tore Biochemistry, Vol. 35, Issue 7 https://doi.org/10.1021/bi9522110	journal	January 1996
A Ni-Fe-Cu Center in a Bifunctional Carbon Monoxide Dehydrogenase/ Acetyl-CoA Synthase Doukov, T. I. Science, Vol. 298, Issue 5593 https://doi.org/10.1126/science.1075843	journal	October 2002
Two Separate One-Electron Steps in the Reductive Activation of the A Cluster in Subunit β of the ACDS Complex in Methanosarcina thermophila ^† Gencic, Simonida; Grahame, David A. Biochemistry, Vol. 47, Issue 20 https://doi.org/10.1021/bi7024035	journal	May 2008
Going beyond Structure: Nickel-Substituted Rubredoxin as a Mechanistic Model for the [NiFe] Hydrogenases Slater, Jeffrey W.; Marguet, Sean C.; Monaco, Haleigh A. Journal of the American Chemical Society, Vol. 140, Issue 32 https://doi.org/10.1021/jacs.8b05194	journal	July 2018
A Biochemical Nickel(I) State Supports Nucleophilic Alkyl Addition: A Roadmap for Methyl Reactivity in Acetyl Coenzyme A Synthase Manesis, Anastasia C.; Musselman, Bradley W.; Keegan, Brenna C. Inorganic Chemistry, Vol. 58, Issue 14 https://doi.org/10.1021/acs.inorgchem.8b03546	journal	February 2019
Inner- and outer-sphere metal coordination in blue copper proteins Warren, Jeffrey J.; Lancaster, Kyle M.; Richards, John H. Journal of Inorganic Biochemistry, Vol. 115 https://doi.org/10.1016/j.jinorgbio.2012.05.002	journal	October 2012
EasySpin, a comprehensive software package for spectral simulation and analysis in EPR Stoll, Stefan; Schweiger, Arthur Journal of Magnetic Resonance, Vol. 178, Issue 1, p. 42-55 https://doi.org/10.1016/j.jmr.2005.08.013	journal	January 2006
Mössbauer Evidence for an Exchange-Coupled {[Fe ₄ S ₄ ] ¹⁺ Ni _p ¹⁺ } A-Cluster in Isolated α Subunits of Acetyl-Coenzyme A Synthase/Carbon Monoxide Dehydrogenase Tan, Xiangshi; Martinho, Marlène; Stubna, Audria Journal of the American Chemical Society, Vol. 130, Issue 21 https://doi.org/10.1021/ja801981h	journal	May 2008
Dinuclear nickel complexes modeling the structure and function of the acetyl CoA synthase active site Ito, Mikinao; Kotera, Mai; Matsumoto, Tsuyoshi Proceedings of the National Academy of Sciences, Vol. 106, Issue 29 https://doi.org/10.1073/pnas.0900433106	journal	July 2009
Evolutionary history of carbon monoxide dehydrogenase/acetyl-CoA synthase, one of the oldest enzymatic complexes Adam, Panagiotis S.; Borrel, Guillaume; Gribaldo, Simonetta Proceedings of the National Academy of Sciences, Vol. 115, Issue 6 https://doi.org/10.1073/pnas.1716667115	journal	January 2018
Kinetics of CO Insertion and Acetyl Group Transfer Steps, and a Model of the Acetyl-CoA Synthase Catalytic Mechanism Tan, Xiangshi; Surovtsev, Ivan V.; Lindahl, Paul A. Journal of the American Chemical Society, Vol. 128, Issue 37 https://doi.org/10.1021/ja0627702	journal	August 2006
Structural and reaction chemistry of nickel complexes in relation to carbon monoxide dehydrogenase: a reaction system simulating acetyl-coenzyme A synthase activity Stavropoulos, Pericles; Muetterties, Mark C.; Carrie, Michel Journal of the American Chemical Society, Vol. 113, Issue 22 https://doi.org/10.1021/ja00022a041	journal	October 1991
Acetate biosynthesis by acetogenic bacteria. Evidence that carbon monoxide dehydrogenase is the condensing enzyme that catalyzes the final steps of the synthesis. Ragsdale, S. W.; Wood, H. G. Journal of Biological Chemistry, Vol. 260, Issue 7 https://doi.org/10.1016/S0021-9258(18)89217-1	journal	April 1985

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