Switchable Chiral Selection of Aspartic Acids by Dynamic States of Brushite

Jiang, Wenge; Pan, Haihua; Zhang, Zhisen; Qiu, S. Roger; Kim, J. Dongun; Xu, Xurong; Tang, Ruikang

doi:10.1021/jacs.7b03116

Title: Switchable Chiral Selection of Aspartic Acids by Dynamic States of Brushite

Journal Article · Thu Jun 15 00:00:00 EDT 2017 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/jacs.7b03116· OSTI ID:1390026

Jiang, Wenge ^[1]; Pan, Haihua ^[2]; Zhang, Zhisen ^[1]; Qiu, S. Roger ^[3]; Kim, J. Dongun ^[4];

^[2];

^[5]

Zhejiang Univ. (China). Center for Biomaterials and Biopathways
Zhejiang Univ. (China). Qiushi Academy for Advanced Studies
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States). Physical and Life Sciences
Rutgers Univ., New Brunswick, NJ (United States). Dept. of Chemistry and Chemical Biology, Inst. of Marine and Coastal Sciences
Zhejiang Univ. (China). Center for Biomaterials and Biopathways, Qiushi Academy for Advanced Studies

Here, we show the chiral recognition and separation of aspartic acid (Asp) enantiomers by achiral brushite due to the asymmetries of their dynamical steps in its nonequilibrium states. Growing brushite has a higher adsorption affinity to d-Asp, while l-Asp is predominant on the dissolving brushite surface. Microstructural characterization reveals that chiral selection is mainly attributed to brushite [101] steps, which exhibit two different configurations during crystal growth and dissolution, respectively, with each preferring a distinct enantiomer due to this asymmetry. Because these transition step configurations have different stabilities, they subsequently result in asymmetric adsorption. Furthermore, by varying free energy barriers through solution thermodynamic driving force (i.e., supersaturation), the dominant nonequilibrium intermediate states can be switched and chiral selection regulated. This finding highlights that the dynamic steps can be vital for chiral selection, which may provide a potential pathway for chirality generation through the dynamic nature.

View Accepted Manuscript (DOE)

Cite

Export

Save

Research Organization:: Lawrence Livermore National Laboratory (LLNL), Livermore, CA (United States)

Sponsoring Organization:: USDOE

Grant/Contract Number:: AC52-07NA27344

OSTI ID:: 1390026

Report Number(s):: LLNL-JRNL-548392; TRN: US1702366

Journal Information:: Journal of the American Chemical Society, Vol. 139, Issue 25; ISSN 0002-7863

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

Citation Metrics:

Cited by: 11 works

Citation information provided by
Web of Science

References (40)

Carbon dioxide on the early earth Walker, James C. G. Origins of Life and Evolution of the Biosphere, Vol. 16, Issue 2 https://doi.org/10.1007/BF01809466	journal	June 1985
Dynamics of Biomineral Formation at the Near-Molecular Level Qiu, S. Roger; Orme, Christine A. Chemical Reviews, Vol. 108, Issue 11 https://doi.org/10.1021/cr800322u	journal	November 2008
Phosphate Solubility and the Cyanate-Mediated Synthesis of Pyrophosphate Hagan, William J.; Parker, Amanda; Steuerwald, Amy Origins of Life and Evolution of Biospheres, Vol. 37, Issue 2 https://doi.org/10.1007/s11084-006-9020-y	journal	November 2006
Enantiomeric Excesses in Meteoritic Amino Acids Cronin, John R.; Pizzarello, Sandra Science, Vol. 275, Issue 5302 https://doi.org/10.1126/science.275.5302.951	journal	February 1997
On the origin of terrestrial homochirality for nucleosides and amino acids Breslow, R.; Cheng, Z. -L. Proceedings of the National Academy of Sciences, Vol. 106, Issue 23 https://doi.org/10.1073/pnas.0904350106	journal	May 2009
Amplification of chirality in two-dimensional enantiomorphous lattices Fasel, Roman; Parschau, Manfred; Ernst, Karl-Heinz Nature, Vol. 439, Issue 7075 https://doi.org/10.1038/nature04419	journal	January 2006
The life span of the biosphere revisited Caldeira, Ken; Kasting, James F. Nature, Vol. 360, Issue 6406 https://doi.org/10.1038/360721a0	journal	December 1992
Cluster Growth Model for Hydroxyapatite Onuma, Kazuo; Ito, Atsuo Chemistry of Materials, Vol. 10, Issue 11 https://doi.org/10.1021/cm980062c	journal	November 1998
Adsorption-induced auto-amplification of enantiomeric excess on an achiral surface Yun, Yongju; Gellman, Andrew J. Nature Chemistry, Vol. 7, Issue 6 https://doi.org/10.1038/nchem.2250	journal	May 2015
Interactions between acidic proteins and crystals: stereochemical requirements in biomineralization. Addadi, L.; Weiner, S. Proceedings of the National Academy of Sciences, Vol. 82, Issue 12 https://doi.org/10.1073/pnas.82.12.4110	journal	June 1985
GROMACS 4: Algorithms for Highly Efficient, Load-Balanced, and Scalable Molecular Simulation Hess, Berk; Kutzner, Carsten; van der Spoel, David Journal of Chemical Theory and Computation, Vol. 4, Issue 3 https://doi.org/10.1021/ct700301q	journal	February 2008
Replica exchange with solute tempering: A method for sampling biological systems in explicit water Liu, P.; Kim, B.; Friesner, R. A. Proceedings of the National Academy of Sciences, Vol. 102, Issue 39 https://doi.org/10.1073/pnas.0506346102	journal	September 2005
Chirality of Living Systems: A Helping Hand from Crystals and Oligopeptides Cintas, Pedro Angewandte Chemie International Edition, Vol. 41, Issue 7 https://doi.org/10.1002/1521-3773(20020402)41:7<1139::AID-ANIE1139>3.0.CO;2-9	journal	April 2002
Impact of Chiral Molecules on the Formation of Biominerals: A Calcium Oxalate Monohydrate Example Cho, Kang Rae; Salter, E. Alan; De Yoreo, James J. Crystal Growth & Design, Vol. 12, Issue 12 https://doi.org/10.1021/cg3009317	journal	November 2012
Growth inhibition of calcium oxalate monohydrate crystal by linear aspartic acid enantiomers investigated by in situatomic force microscopy Cho, Kang R.; Salter, E. Alan; De Yoreo, James J. CrystEngComm, Vol. 15, Issue 1 https://doi.org/10.1039/C2CE25936B	journal	January 2013
Rethinking early Earth phosphorus geochemistry Pasek, M. A. Proceedings of the National Academy of Sciences, Vol. 105, Issue 3 https://doi.org/10.1073/pnas.0708205105	journal	January 2008
Biological and Medical Significance of Calcium Phosphates Dorozhkin, Sergey V.; Epple, Matthias Angewandte Chemie International Edition, Vol. 41, Issue 17 https://doi.org/10.1002/1521-3773(20020902)41:17<3130::AID-ANIE3130>3.0.CO;2-1	journal	September 2002
Comparison of simple potential functions for simulating liquid water Jorgensen, William L.; Chandrasekhar, Jayaraman; Madura, Jeffry D. The Journal of Chemical Physics, Vol. 79, Issue 2 https://doi.org/10.1063/1.445869	journal	July 1983
Chirality and life Bonner, William A. Origins of Life and Evolution of the Biosphere, Vol. 25, Issue 1-3 https://doi.org/10.1007/BF01581581	journal	June 1995
Control of Biomineralization Dynamics by Interfacial Energies Tang, Ruikang; Darragh, Molly; Orme, Christine A. Angewandte Chemie International Edition, Vol. 44, Issue 24 https://doi.org/10.1002/anie.200500153	journal	June 2005
Climatic consequences of very high carbon dioxide levels in the earth's early atmosphere Kasting, J.; Ackerman, T. Science, Vol. 234, Issue 4782 https://doi.org/10.1126/science.11539665	journal	December 1986
Asymmetric Adsorption of Alanine by Quartz Bonner, W. A.; Kavasmaneck, P. R.; Martin, F. S. Science, Vol. 186, Issue 4159 https://doi.org/10.1126/science.186.4159.143	journal	October 1974
Formation of chiral morphologies through selective binding of amino acids to calcite surface steps Orme, C. A.; Noy, A.; Wierzbicki, A. Nature, Vol. 411, Issue 6839 https://doi.org/10.1038/35081034	journal	June 2001
Theoretical analysis of specific evolution of some faces of plant COM crystals Prywer, Jolanta CrystEngComm, Vol. 11, Issue 1 https://doi.org/10.1039/B802023J	journal	January 2009
Presidential Address to the Mineralogical Society of America, Salt Lake City, October 18, 2005: Mineral surfaces and the prebiotic selection and organization of biomolecules Hazen, R. M. American Mineralogist, Vol. 91, Issue 11-12 https://doi.org/10.2138/am.2006.2289	journal	November 2006
Surface structure of potassium dichromate (KBC) crystals Reedijk, M. F.; Arsic, J.; Kaminski, D. Surface Science, Vol. 526, Issue 1-2 https://doi.org/10.1016/S0039-6028(02)02595-5	journal	February 2003
Controlling Crystal Surface Termination by Cleavage Direction Plomp, M.; van Enckevort, W. J. P.; Vlieg, E. Physical Review Letters, Vol. 86, Issue 22 https://doi.org/10.1103/PhysRevLett.86.5070	journal	May 2001
How Did Life Begin? Fox, S. W. Science, Vol. 132, Issue 3421 https://doi.org/10.1126/science.132.3421.200	journal	July 1960
Selective adsorption of L- and D-amino acids on calcite: Implications for biochemical homochirality Hazen, R. M.; Filley, T. R.; Goodfriend, G. A. Proceedings of the National Academy of Sciences, Vol. 98, Issue 10 https://doi.org/10.1073/pnas.101085998	journal	May 2001
Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids Jorgensen, William L.; Maxwell, David S.; Tirado-Rives, Julian Journal of the American Chemical Society, Vol. 118, Issue 45 https://doi.org/10.1021/ja9621760	journal	January 1996
Chiral selection on inorganic crystalline surfaces Hazen, Robert M.; Sholl, David S. Nature Materials, Vol. 2, Issue 6 https://doi.org/10.1038/nmat879	journal	June 2003
THE weighted histogram analysis method for free-energy calculations on biomolecules. I. The method Kumar, Shankar; Rosenberg, John M.; Bouzida, Djamal Journal of Computational Chemistry, Vol. 13, Issue 8 https://doi.org/10.1002/jcc.540130812	journal	October 1992
Chiral Amplification of Oligopeptides in Two-Dimensional Crystalline Self-Assemblies on Water Zepik, H. Science, Vol. 295, Issue 5558 https://doi.org/10.1126/science.1065625	journal	January 2002
Dissolution kinetics of dicalcium phosphate dihydrate under pseudophysiological conditions Kanzaki, Noriko; Onuma, Kazuo; Treboux, Gabin Journal of Crystal Growth, Vol. 235, Issue 1-4 https://doi.org/10.1016/S0022-0248(01)01771-7	journal	February 2002
A Production of Amino Acids Under Possible Primitive Earth Conditions Miller, S. L. Science, Vol. 117, Issue 3046 https://doi.org/10.1126/science.117.3046.528	journal	May 1953
Investigation of a growth unit of hydroxyapatite crystal from the measurements of step kinetics Onuma, Kazuo; Ito, Atsuo; Tateishi, Tetsuya Journal of Crystal Growth, Vol. 167, Issue 3-4 https://doi.org/10.1016/0022-0248(96)00421-6	journal	October 1996
The role of hydrogen bonding in the thermal expansion and dehydration of brushite, di-calcium phosphate dihydrate Schofield, P. F.; Knight, K. S.; Houwen, J. A. M. van der Physics and Chemistry of Minerals, Vol. 31, Issue 9 https://doi.org/10.1007/s00269-004-0419-6	journal	December 2004
Molecular mechanisms of crystallization impacting calcium phosphate cements Giocondi, Jennifer L.; El-Dasher, Bassem S.; Nancollas, George H. Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 368, Issue 1917 https://doi.org/10.1098/rsta.2010.0006	journal	April 2010
Liquid ordering at the Brushite- ${010}$ –water interface Arsic, J.; Kaminski, D.; Poodt, P. Physical Review B, Vol. 69, Issue 24 https://doi.org/10.1103/PhysRevB.69.245406	journal	June 2004
V. Über die Symmetrie der Krystalle von Kaliumdichromat Schubnikow, A. Zeitschrift für Kristallographie - Crystalline Materials, Vol. 50, Issue 1-6 https://doi.org/10.1524/zkri.1912.50.1.19	journal	December 1912

Cited By (5)

Chiral biomineralized structures and their biomimetic synthesis Jiang, Wenge; Yi, Xing; McKee, Marc D. Materials Horizons, Vol. 6, Issue 10 https://doi.org/10.1039/c9mh00431a	journal	January 2019
Macroscopic Chiral Recognition by Calix[4]arene‐Based Host–Guest Interactions Quan, Jiaxin; Nie, Guanrong; Xue, Hong Chemistry – A European Journal, Vol. 24, Issue 58 https://doi.org/10.1002/chem.201803564	journal	September 2018
Chiral switching in biomineral suprastructures induced by homochiral l-amino acid Jiang, Wenge; Pacella, Michael S.; Vali, Hojatollah Science Advances, Vol. 4, Issue 8 https://doi.org/10.1126/sciadv.aas9819	journal	August 2018
Homochirality in biomineral suprastructures induced by assembly of single-enantiomer amino acids from a nonracemic mixture Jiang, Wenge; Athanasiadou, Dimitra; Zhang, Shaodong Nature Communications, Vol. 10, Issue 1 https://doi.org/10.1038/s41467-019-10383-x	journal	May 2019
Water Structure, Dynamics and Ion Adsorption at the Aqueous {010} Brushite Surface Garcia, Natalya; Raiteri, Paolo; Vlieg, Elias Minerals, Vol. 8, Issue 8 https://doi.org/10.3390/min8080334	journal	August 2018

Similar Records

Molecular-level Design of Heterogeneous Chiral Catalysts

Technical Report · Sun Apr 28 00:00:00 EDT 2013 · OSTI ID:1390026

Gellman, Andrew John; Sholl, David S.; Tysoe, Wilfred T.; +1 more

Photoinduced molecular chirality probed by ultrafast resonant X-ray spectroscopy

Journal Article · Sat Jul 01 00:00:00 EDT 2017 · Structural Dynamics · OSTI ID:1390026

Rouxel, Jérémy R.; Kowalewski, Markus; Mukamel, Shaul

Intrinsic Chirality and Prochirality at Air/R-(+)- and S-(-)-Limonene Interfaces: Spectral Signatures with Interference Chiral Sum-Frequency Generation Vibrational Spectroscopy

Journal Article · Wed Jun 04 00:00:00 EDT 2014 · Chirality, 26(9):509-520 · OSTI ID:1390026

Fu, Li; Zhang, Yun; Wei, Zhehao; +1 more

Related Subjects

36 MATERIALS SCIENCE

Title: Switchable Chiral Selection of Aspartic Acids by Dynamic States of Brushite

Citation Formats

References (40)

Cited By (5)

Similar Records

Related Subjects