Home / Articles / The origin of homochirality in nature: a possible version

The origin of homochirality in nature: a possible version

Valerii Alekseevich Pavlov 1
Valerii Alekseevich Pavlov
, 
Evgenii Ivanovich Klabunovskii 1
Evgenii Ivanovich Klabunovskii
1 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow
10.1070/RCR4444
Published 30 November 2014
Communication , Volume 84, Issue 2, 121-133
13
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Pavlov V. A., Klabunovskii E. I. The origin of homochirality in nature: a possible version // Russian Chemical Reviews. 2015. Vol. 84. No. 2. pp. 121-133.
GOST all authors (up to 50)
Copy cite
Pavlov V. A., Klabunovskii E. I. The origin of homochirality in nature: a possible version // Russian Chemical Reviews. 2015. Vol. 84. No. 2. pp. 121-133.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RCR4444
UR - https://rcr.colab.ws/publications/10.1070/RCR4444
TI - The origin of homochirality in nature: a possible version
T2 - Russian Chemical Reviews
AU - Pavlov, Valerii Alekseevich
AU - Klabunovskii, Evgenii Ivanovich
PY - 2015
DA - 2014/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 121-133
IS - 2
VL - 84
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{2015_Pavlov,
author = {Valerii Alekseevich Pavlov and Evgenii Ivanovich Klabunovskii},
title = {The origin of homochirality in nature: a possible version},
journal = {Russian Chemical Reviews},
year = {2015},
volume = {84},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4444},
number = {2},
pages = {121--133},
doi = {10.1070/RCR4444}
}
MLA
Cite this
MLA
Copy cite
Pavlov, Valerii Alekseevich, and Evgenii Ivanovich Klabunovskii. “The origin of homochirality in nature: a possible version.” Russian Chemical Reviews, vol. 84, no. 2, Nov. 2015, pp. 121-133. https://rcr.colab.ws/publications/10.1070/RCR4444.
Views / Visits / Downloads
22 / 22 / 8

Abstract

The proper axial rotation and right-handed helical orbital rotation of Earth are the simplest and persistent factors of chiral influence on the Earth. These types of motion are treated as basic to the selection of L-amino acids and D-sugars (homochirality) as 'building blocks' for constructing right-handed helical biomacromolecules. The role of agent for transfer of chiral influence of the factors mentioned above on the molecular level can be played by tides and wind waves. The rise and fall of the waves leads to formation of mainly right-handed helical water associates that favour the formation of right-handed helical biomolecules. Biological indications of the existence of such water associates are discussed.

The bibliography includes 175 references.

References

1.
Homochirality Origin in Nature: Possible Versions
Pavlov V., Klabunovskii E.
Current Organic Chemistry , 2013
2.
Amino Acids and the Asymmetry of Life
Meierhenrich U.J.
European Review , 2013
4.
Chirality, photochemistry and the detection of amino acids in interstellar ice analogues and comets
Evans A.C., Meinert C., Giri C., Goesmann F., Meierhenrich U.J.
Chemical Society Reviews , 2012
7.
8
V. N. Kondrat'ev
"Kinetika Reaktsii v Gazovoi Faze" (Kinetics of Reactions in the Gas Phase) , 1959
9.
Origin of Homochirality in Biosystems
Toxvaerd S.
International Journal of Molecular Sciences , 2009
10.
11
T. T. Bannister
Diss. Abstr. , 1959
13.
Emergence of homochirality in far-from-equilibrium systems: Mechanisms and role in prebiotic chemistry
Plasson R., Kondepudi D.K., Bersini H., Commeyras A., Asakura K.
Chirality , 2007
14.
Parity Violating Energetic Difference and Enantiomorphous Crystalsp-Caveats; Reinvestigation of Tyrosine Crystallization
Lahav M., Weissbuch I., Shavit E., Reiner C., Nicholson G.J., Schurig V.
Origins of Life and Evolution of Biospheres , 2006
16.
Asymmetric Photoreactions as the Origin of Biomolecular Homochirality: A Critical Review
Jorissen A., Cerf C.
Origins of Life and Evolution of Biospheres , 2002
17.
Origin of organic molecules and biomolecular homochirality
Podlech J.
Cellular and Molecular Life Sciences , 2001
18.
10.1002/(SICI)1521-3773(19991203)38:23<3418::AID-ANIE3418>3.0.CO;2-V
19.
Chiral Autocatalysis, Spontaneous Symmetry Breaking, and Stochastic Behavior
Kondepudi D.K., Asakura K.
Accounts of Chemical Research , 2001
20.
Chirality in Chemistry
Prelog V.
Science , 1976
22.
A new definition of life
Carroll J.D.
Chirality , 2009
23.
24
M. S. Ashkinazi
Dokl. Akad. Nauk SSSR , 1951
24.
25
G. W. Robinson
J. Chem. Phys. , 1955
27.
Spontaneous breaking of mirror symmetry in nature and the origin of life
Gol'danskiĭ V.I., Kuz'min V.V.
Soviet Physics Uspekhi , 1989
28.
Spontaneous breaking of mirror symmetry in nature and the origin of life
Gol'danskii V.I., Kuz'min V.V.
Uspekhi Fizicheskih Nauk , 2010
29.
Chirality and cold origin of life
Goldanskii V., KUZMIN V.V.
Nature , 1991
31.
32
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
32.
33
M. B. Neiman
"Issledovanie Mekhanizma Okisleniya Butana" (Research on the Mechanism of the Oxidation of Butane) , 1939
33.
First molecules, biological chirality, origin(s) of life
Caglioti L., Micskei K., Pályi G.
Chirality , 2010
34.
The origin of the biologically coded amino acids
Cleaves II H.J.
Journal of Theoretical Biology , 2010
35.
36
J. Billon
Bull. Soc. chim. France , 1960
37.
Production of Some Organic Compounds under Possible Primitive Earth Conditions1
Miller S.L.
Journal of the American Chemical Society , 1955
38.
Prebiotic Synthesis of Hydrophobic and Protein Amino Acids
Ring D., Wolman Y., Friedmann N., Miller S.L.
Proceedings of the National Academy of Sciences of the United States of America , 1972
39.
Reasons for the occurrence of the twenty coded protein amino acids
Weber A.L., Miller S.L.
Journal of Molecular Evolution , 1981
40.
The spark discharge synthesis of amino acids from various hydrocarbons
Ring D., Miller S.L.
Origins of Life and Evolution of Biospheres , 1984
42.
43
N. Bunge
Ber. Deutsch. Chem. Ges. , 1870
44.
45
W. Hendrich
Roczniki Chemii , 1958
45.
Shock Synthesis of Amino Acids in Simulated Primitive Environments
Bar-Nun A., Bar-Nun N., Bauer S.H., Sagan C.
Science , 1970
47.
48
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1955
48.
Direct amination of carboxylic acids with ammonia by electric discharge against aqueous solution
Harada K., Hasegawa N., Shimoyama A.
Origins of Life and Evolution of Biospheres , 1984
49.
Novel formation of ?-amino acid from ?-oxo acids and ammonia in an aqueous medium
Yanagawa H., Makino Y., Sato K., Nishizawa M., Egami F.
Origins of Life and Evolution of Biospheres , 1984
50.
Amino acid pairing
Root-Bernstein R.S.
Journal of Theoretical Biology , 1982
51.
Protein replication by amino acid pairing
Root-Bernstein R.S.
Journal of Theoretical Biology , 1983
52.
Compositional complementarity and prebiotic ecology in the origin of life
Hunding A., Kepes F., Lancet D., Minsky A., Norris V., Raine D., Sriram K., Root-Bernstein R.
BioEssays , 2006
53.
Light-Induced Peptide Replication Controls Logic Operations in Small Networks
Dadon Z., Samiappan M., Safranchik E.Y., Ashkenasy G.
Chemistry - A European Journal , 2010
54.
Sequence generation in prebiological peptide synthesis
Steinman G.
Archives of Biochemistry and Biophysics , 1967
55.
Prebiotic synthesis of biopolymers on inorganic templates
Katchalsky A.
Die Naturwissenschaften , 1973
56.
Prebiotic Activation Processes
LOHRMANN R., ORGEL L.E.
Nature , 1973
58.
About a Formamide-Based Origin of Informational Polymers: Syntheses of Nucleobases and Favourable Thermodynamic Niches for Early Polymers
Saladino R., Crestini C., Ciciriello F., Costanzo G., Di Mauro E.
Origins of Life and Evolution of Biospheres , 2006
59.
Nucleic Acids Bind to Nanoparticulate iron (II) Monosulphide in Aqueous Solutions
Hatton B., Rickard D.
Origins of Life and Evolution of Biospheres , 2008
61.
The prebiotic synthesis of deoxythymidine oligonucleotides
Odom D.G., Brady J.T.
Journal of Molecular Evolution , 1975
62.
Zur Kondensation von Aminoacyl-adenylaten
Krampitz G., Baars S., Haas W., Kempfle M.
Die Naturwissenschaften , 1969
63.
Peptide Nucleic Acids and the Origin of Life
Nielsen P.
Chemistry and Biodiversity , 2007
64.
Peptide nucleic acids and prebiotic chemistry
Miller S.L.
Nature Structural Biology , 1997
65.
pH profile of the adsorption of nucleotides onto montmorillonite
Lawless J.G., Banin A., Church F.M., Mazzurco J., Huff R., Kao J., Cook A., Lowe T., Orenberg J.B., Edelson E.
Origins of Life and Evolution of Biospheres , 1985
66.
Prebiotic phosphorylation. II-nucleotide synthesis in the reaction system apatite-cyanogen-water
Schwartz A.W., van der Veen M., Bisseling T., Chittenden G.J.
BioSystems , 1973
67.
Supramolecular Porous Network Formed by Molecular Recognition between Chemically Modified Nucleobases Guanine and Cytosine
Xu W., Wang J., Jacobsen M.F., Mura M., Yu M., Kelly R.E., Meng Q., Laegsgaard E., Stensgaard I., Linderoth T.R., Kjems J., Kantorovich L.N., Gothelf K.V., Besenbacher F.
Angewandte Chemie - International Edition , 2010
68.
Model for Origin of Monosaccharides
GABEL N.W., PONNAMPERUMA C.
Nature , 1967
69.
Synthesis of Carbohydrates in Mineral-Guided Prebiotic Cycles
Kim H., Ricardo A., Illangkoon H.I., Kim M.J., Carrigan M.A., Frye F., Benner S.A.
Journal of the American Chemical Society , 2011
73.
Adsorption of nucleic acid components on rutile (TiO(2)) surfaces.
Cleaves H.J., Jonsson C.M., Jonsson C.L., Sverjensky D.A., Hazen R.M.
Astrobiology , 2010
74.
Asymmetric Catalysis Special Feature Part II: Asymmetric autocatalysis and its implications for the origin of homochirality
Blackmond D.G.
Proceedings of the National Academy of Sciences of the United States of America , 2004
76.
Chirality Amplification – The Accumulation Principle Revisited
Bonner W.A.
Origins of Life and Evolution of Biospheres , 1999
77.
Enantioselective Automultiplication of Chiral Molecules by Asymmetric Autocatalysis
Soai K., Shibata T., Sato I.
Accounts of Chemical Research , 2000
80.
Dynamic Photoswitching of Helical Inversion in Liquid Crystals Containing Photoresponsive Axially Chiral Dopants
Hayasaka H., Miyashita T., Nakayama M., Kuwada K., Akagi K.
Journal of the American Chemical Society , 2012
81.
Enantioselective hydrogenation in a cholesteric liquid crystal as a chiral matrix
Pavlov V.A., Spitsyna N.I., Klabunovskii E.I.
Russian Chemical Bulletin , 1982
82.
83
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
83.
Enantioselective hydrogenation in cholesteryl tridecanoate as a chiral liquid-crystalline matrix
Pavlov V.A., Spitsyna N.I., Klabunovskii E.I.
Russian Chemical Bulletin , 1983
84.
85
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1947
85.
Photochirogenesis: Photochemical models on the absolute asymmetric formation of amino acids in interstellar space
Meinert C., de Marcellus P., Le Sergeant dʼHendecourt L., Nahon L., Jones N.C., Hoffmann S.V., Bredehöft J.H., Meierhenrich U.J.
Physics of Life Reviews , 2011
86.
An astrophysically-relevant mechanism for amino acid enantiomer enrichment
Fletcher S.P., Jagt R.B., Feringa B.L.
Chemical Communications , 2007
87.
Supernovae and life
RUBENSTEIN E., BONNER W.A., NOYES H.P., BROWN G.S.
Nature , 1983
88.
Asymmetric Photolysis with Elliptically Polarized Light
Bonner W.A.
Origins of Life and Evolution of Biospheres , 2000
89.
Asymmetric photolysis of (RS)-leucine with circularly polarized ultraviolet light
Flores J.J., Bonner W.A., Massey G.A.
Journal of the American Chemical Society , 1977
90.
UV Circular Polarisation in Star Formation Regions: The Origin of Homochirality?
Lucas P.W., Hough J.H., Bailey J., Chrysostomou A., Gledhill T.M., McCall A.
Origins of Life and Evolution of Biospheres , 2005
92.
Question of Parity Conservation in Weak Interactions
Lee T.D., Yang C.N.
Physical Review A , 1956
95.
Detection of a dipole in the handedness of spiral galaxies with redshifts z∼0.04
Longo M.J.
Physics Letters, Section B: Nuclear, Elementary Particle and High-Energy Physics , 2011
96.
True and false chirality and absolute asymmetric synthesis
Barron L.D.
Journal of the American Chemical Society , 1986
100.
Asymmetric induction in reactions catalyzed by metal complexes
Pavlov V.A., Pavlova T.N.
Russian Chemical Reviews , 2012
101.
Asymmetric transfer hydrogenation of C=O and C=N bonds
Palmer M.J., Wills M.
Tetrahedron Asymmetry , 1999
102.
Asymmetric hydrogen transfer reactions promoted by homogeneous transition metal catalysts
Zassinovich G., Mestroni G., Gladiali S.
Chemical Reviews , 1992
104.
Asymmetric transfer hydrogenation of ketones catalyzed by phosphine-rhodium(I) and -iridium(I) complexes
Spogliarich R., Kašpar J., Graziani M., Morandini F.
Journal of Organometallic Chemistry , 1986
110.
Chiral pyrrolidine derivatives as catalysts in the enantioselective addition of diethylzinc to aldehydes
Yang X., Shen J., Da C., Wang R., Choi M.C., Yang L., Wong K.
Tetrahedron Asymmetry , 1999
111.
10.1002/(SICI)1521-3773(19990215)38:4<497::AID-ANIE497>3.0.CO;2-G
116.
A New Bifunctional Asymmetric Catalysis:  An Efficient Catalytic Asymmetric Cyanosilylation of Aldehydes
Hamashima Y., Sawada D., Kanai M., Shibasaki M.
Journal of the American Chemical Society , 1999
119.
A Novel Chiral (salen)AlIII Complex Catalyzed Asymmetric Cyanosilylation of Aldehydes
Zeng Z., Zhao G., Zhou Z., Tang C.
European Journal of Organic Chemistry , 2008
122.
Chiral Bis(imidazolidine)pyridine−Cu(OTf)2: Catalytic Asymmetric Endo-Selective [3 + 2] Cycloaddition of Imino Esters with Nitroalkenes
Arai T., Mishiro A., Yokoyama N., Suzuki K., Sato H.
Journal of the American Chemical Society , 2010
123.
New Ruthenium Catalysts for Asymmetric Transfer Hydrogenation of Prochiral Ketones
Enthaler S., Hagemann B., Bhor S., Anilkumar G., Tse M.K., Bitterlich B., Junge K., Erre G., Beller M.
Advanced Synthesis and Catalysis , 2007
124.
Mechanism of the Enantioselective Oxidation of Racemic Secondary Alcohols Catalyzed by Chiral Mn(III)−Salen Complexes
Brown M.K., Blewett M.M., Colombe J.R., Corey E.J.
Journal of the American Chemical Society , 2010
125.
126
J. Wiemannand Ch. Clachet
Compt. rend. , 1948
130.
131
N. Thooi
Compt. rend. , 1958
131.
132
G. Shima
Kyoto Univ. , 1929
132.
133
C. Wilson
Trans. Electrochem. Soc. , 1941
133.
The Fractal Geometry of Nature
Mandelbrot B.B., Wheeler J.A.
American Journal of Physics , 1983
134.
135
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1945
135.
Voyager 1 Explores the Termination Shock Region and the Heliosheath Beyond
Stone E.C., Cummings A.C., McDonald F.B., Heikkila B.C., Lal N., Webber W.R.
Science , 2005
136.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
137.
138
S. Ono
J. Chem. Soc. Japan , 1957
138.
Voyager 1 in the Foreshock, Termination Shock, and Heliosheath
Decker R.B., Krimigis S.M., Roelof E.C., Hill M.E., Armstrong T.P., Gloeckler G., Hamilton D.C., Lanzerotti L.J.
Science , 2005
139.
Is the solar system entering a nearby interstellar cloud
Vidal-Madjar A., Laurent C., Bruston P., Audouze J.
Astrophysical Journal , 2002
140.
Thermal formation of serine octamer ions
Takáts Z., Cooks R.G.
Chemical Communications , 2004
141.
Serine Octamers: Cluster Formation, Reactions, and Implications for Biomolecule Homochirality
Nanita S.C., Cooks R.G.
Angewandte Chemie - International Edition , 2006
142.
Serine sublimes with spontaneous chiral amplification
Perry R.H., Wu C., Nefliu M., Cooks R.G.
Chemical Communications , 2007
143.
Chemical and immunochemical studies on the structure of four snail galactans
Bretting H., Whittaker N.F., Kabat E.A., Königsmann-Lange K., Thiem H.
Carbohydrate Research , 1981
144.
145
Friedl.
145.
146
V. V. Korshak
Dokl. Akad. Nauk SSSR , 1952
146.
The double-helical molecular structure of crystalline a-amylose
Hsien-Chih H.W., Sarko A.
Carbohydrate Research , 1978
148.
Conformation of the “V” amylose helix
French A., Zaslow B.
Journal of the Chemical Society Chemical Communications , 1972
149.
Crystal structure of the koh-amylose complex
Sarko A., Biloski A.
Carbohydrate Research , 1980
150.
Molecular and Crystal Structure of 7-Fold V-Amylose Complexed with 2-Propanol
Nishiyama Y., Mazeau K., Morin M., Cardoso M.B., Chanzy H., Putaux J.
Macromolecules , 2010
151.
Amylose folding under the influence of lipids
López C.A., de Vries A.H., Marrink S.J.
Carbohydrate Research , 2012
152.
Conformational properties of two exopolysaccharides produced by Inquilinus limosus, a cystic fibrosis lung pathogen
Kuttel M., Ravenscroft N., Foschiatti M., Cescutti P., Rizzo R.
Carbohydrate Research , 2012
157.
Multiple Conformation Transitions of Triple Helical Lentinan in DMSO/Water by Microcalorimetry
Wang X., Zhang Y., Zhang L., Ding Y.
Journal of Physical Chemistry B , 2009
158.
Guar Gum and Scleroglucan Interactions with Borax: Experimental and Theoretical Studies of an Unexpected Similarity
Bocchinfuso G., Mazzuca C., Sandolo C., Margheritelli S., Alhaique F., Coviello T., Palleschi A.
Journal of Physical Chemistry B , 2010
159.
Molecular Dynamics Studies of Side Chain Effect on the β-1,3-d-Glucan Triple Helix in Aqueous Solution
Okobira T., Miyoshi K., Uezu K., Sakurai K., Shinkai S.
Biomacromolecules , 2008
163.
Supercoiling in circular triple-helical polysaccharides
Stokke B.T., Elgsaeter A., Brant D.A., Kitamura S.
Macromolecules , 1991
165.
Correlation between the antitumor activity of a polysaccharide schizophyllan and its triple-helical conformation in dilute aqueous solution.
Yanaki T., Ito W., Tabata K., Kojima T., Norisuye T., Takano N., Fujita H.
Biophysical Chemistry , 1983
167.
The effect of glycosylation with dextran chains of differing lengths on the thermal aggregation of β-conglycinin and glycinin
Xu C., Yang X., Yu S., Qi J., Guo R., Sun W., Yao Y., Zhao M.
Food Research International , 2010
169.
A putative lipoprotein ofSphingomonassp. strain A1 binds alginate rather than a lipid moiety
He J., Ochiai A., Fukuda Y., Hashimoto W., Murata K.
FEMS Microbiology Letters , 2008
170.
Crystal structure of bacterial cell-surface alginate-binding protein with an M75 peptidase motif
Maruyama Y., Ochiai A., Mikami B., Hashimoto W., Murata K.
Biochemical and Biophysical Research Communications , 2011
171.
Polysaccharide binding sites in hyaluronate lyase - crystal structures of native phage-encoded hyaluronate lyase and its complexes with ascorbic acid and lactose
Mishra P., Prem Kumar R., Ethayathulla A.S., Singh N., Sharma S., Perbandt M., Betzel C., Kaur P., Srinivasan A., Bhakuni V., Singh T.P.
FEBS Journal , 2009
172.
173
Friedl.
173.
174
S. Calvert
India Rubber Tire Rev. , 1926
175.
176
G. V. Samsonov
"Metody Ispytaniya na Mikrotverdost' i Pribory" (Methods of Microhardness Testing and Apparatus) , 1965
176.
177
J. Henry
Proc. R. Irish Acad. , 1945
177.
178
1946
178.
179
Chem. Abs. , 1947
179.
180
1946