scholarly journals Homochirality Is Originated from Handedness of Helices

2020 ◽  
Author(s):  
Shubin Liu
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Electrostatic Interactions ◽  
Alpha Helix ◽  
Root Cause ◽  
Macromolecular Assembly ◽  
Nucleotide Sugars ◽  
Cooperativity Effects ◽  
Natural Amino Acids ◽  
Origin Of Homochirality

Homochirality is a common feature of amino acids and carbohydrates, whose origin is still unknown. For example, 19 of 20 natural amino acids are L-chiral but deoxyribose sugars in DNA are always D-chiral. Meanwhile, right-handed helices are ubiquitous in nature. Are these two phenomena intrinsically correlated? Here, we propose that homochirality of amino acids and nucleotide sugars is originated from the handedness of helices. We show that right-handed 3<sub>10-</sub>helix and alpha-helix favor the L-chiral form for amino acids, but for deoxyribose sugars right-handed helices prefer the D-chiral form instead. Our analyses unveil that there exist strong cooperativity effects dominated by electrostatic interactions. This work not only resolves the mystery of homochirality by providing a unified explanation for the origin of homochirality in proteins and DNA using helical secondary structures as the root cause, but also ratifies the Principle of Chirality Hierarchy, where chirality of a higher hierarchy dictates that of lower ones. Possible applications of the present work to asymmetric synthesis and macromolecular assembly are discussed.

scholarly journals Homochirality Is Originated from Handedness of Helices

2020 ◽  
Author(s):  
Shubin Liu
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Electrostatic Interactions ◽  
Alpha Helix ◽  
Root Cause ◽  
Macromolecular Assembly ◽  
Nucleotide Sugars ◽  
Cooperativity Effects ◽  
Natural Amino Acids ◽  
Origin Of Homochirality

Homochirality is a common feature of amino acids and carbohydrates, whose origin is still unknown. For example, 19 of 20 natural amino acids are L-chiral but deoxyribose sugars in DNA are always D-chiral. Meanwhile, right-handed helices are ubiquitous in nature. Are these two phenomena intrinsically correlated? Here, we propose that homochirality of amino acids and nucleotide sugars is originated from the handedness of helices. We show that right-handed 3<sub>10-</sub>helix and alpha-helix favor the L-chiral form for amino acids, but for deoxyribose sugars right-handed helices prefer the D-chiral form instead. Our analyses unveil that there exist strong cooperativity effects dominated by electrostatic interactions. This work not only resolves the mystery of homochirality by providing a unified explanation for the origin of homochirality in proteins and DNA using helical secondary structures as the root cause, but also ratifies the Principle of Chirality Hierarchy, where chirality of a higher hierarchy dictates that of lower ones. Possible applications of the present work to asymmetric synthesis and macromolecular assembly are discussed.

ChemInform Abstract: Synthesis of (S)-N-tert-Butoxycarbonyl-N,O-isopropylidene-α-methylserinal: A Potential Building Block for the Asymmetric Synthesis of Non-Natural Amino Acids.

ChemInform ◽  
2010 ◽  
Vol 30 (14) ◽  
pp. no-no
Author(s):  
Myriam Alias ◽  
Carlos Cativiela ◽  
Maria D. Diaz-de-Villegas ◽  
Jose A. Galvez ◽  
Yolanda Lapena
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Building Block ◽  
Natural Amino Acids

Synthesis of (S)-N-tert-butoxycarbonyl-N,O-isopropylidene-α-methylserinal: A potential building block for the asymmetric synthesis of non-natural amino acids

Tetrahedron ◽  
1998 ◽  
Vol 54 (49) ◽  
pp. 14963-14974 ◽  
Author(s):  
Myriam Alías ◽  
Carlos Cativiela ◽  
María D. Díaz-de-Villegas ◽  
JoséA. Gálvez ◽  
Yolanda Lapeña
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Building Block ◽  
Natural Amino Acids

Asymmetric synthesis of amino acids by Cr(II) complexes of natural amino acids

2003 ◽  
Vol 682 (1-2) ◽  
pp. 143-148 ◽  
Author(s):  
Károly Micskei ◽  
Orsolya Holczknecht ◽  
Csongor Hajdu ◽  
Tamás Patonay ◽  
Valér Marchis ◽  
...  
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Natural Amino Acids

Rational engineering of Acinetobacter tandoii glutamate dehydrogenase for asymmetric synthesis of L-homoalanine through biocatalytic cascades

2021 ◽  
Author(s):  
Liuzhu Wang ◽  
Shiqing Diao ◽  
Yangyang Sun ◽  
Shuiqin Jiang ◽  
Yan Liu ◽  
...  
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Glutamate Dehydrogenase ◽  
Building Block ◽  
Chiral Drugs ◽  
Rational Engineering ◽  
Natural Amino Acids

L-Homoalanine, a useful building block for the synthesis of several chiral drugs, is generally synthesized through biocascades using natural amino acids as cheap starting reactants. However, the addition of expensive...

Amino acids and Peptides Organocatalysts: A Brief Overview on Its Evolution and Applications in Organic Asymmetric Synthesis

2020 ◽  
Vol 07 ◽  
Author(s):  
Kantharaju Kamanna
Keyword(s):  
Amino Acids ◽  
Asymmetric Synthesis ◽  
Stereoselective Synthesis ◽  
Flow Reactor ◽  
Industrial Applications ◽  
Organic Transformations ◽  
Heterogeneous Catalytic ◽  
Heterogeneous Phase ◽  
Inorganic Supports ◽  
Natural Amino Acids

: This review highlights the application of biopolymers of natural α-amino acids and its derived wild type peptides employed as an organocatalysis for the asymmetric synthesis published by researchers across the globe is described. The α-amino acids with L-stereochemistry are available commercial in pure form are played crucial role in enantioselective chiral molecule synthesis. Out of twenty natural amino acids, only one secondary amine containing proline amino acid exhibited revolution in the field of orgnocatalysis, because of its rigid structure and formation of an imine like transition state during the reaction lead more stereoselectivity. Hence, it is referred to as a simple enzyme in organocatalyst. Further discussed chiral organic molecule synthesis by employing oligopeptides derived from the natural amino acids as a robust biocatalyst replaced enzyme catalysts. The peptide includes di-, tri, tetra-, penta- and oligopeptide derived demonstrated as a potential organocatalysts, whose reaction activity and mechanistic pathways are reviewed. Several choice of families of these organocatalysts permit chemist to achieve facile and efficient stereoselective synthesis of many complex natural products with optically pure isomer. Subsequently, researcher developed green and sustainable heterogeneous catalytic system containing organocatalyst immobilized onto solid inorganic supports or porous materials, and is responsible for accelerating the reaction through heterogeneous phase. The developed heterogeneous organocatalysts-MOFs found to be used easier and employed for bulk production and flow reactor synthesis. This review compiled many outstanding discoveries in organocatalysts derived amino acids and it’s heterogenized on to MOFs together role of the organocatalysis in many organic transformations in academic and industrial applications are covered.

Homochirality as the Signature of Extra-Terrestrial Life

1997 ◽  
Vol 161 ◽  
pp. 505-510
Author(s):  
Alexandra J. MacDermott ◽  
Laurence D. Barron ◽  
Andrè Brack ◽  
Thomas Buhse ◽  
John R. Cronin ◽  
...  
Keyword(s):  
Amino Acids ◽  
Protein Synthesis ◽  
Optical Rotation ◽  
Physical Origin ◽  
Natural Choice ◽  
Rosetta Mission ◽  
Terrestrial Life ◽  
Subsurface Layers ◽  
Solar System Bodies ◽  
Origin Of Homochirality

AbstractThe most characteristic hallmark of life is its homochirality: all biomolecules are usually of one hand, e.g. on Earth life uses only L-amino acids for protein synthesis and not their D mirror images. We therefore suggest that a search for extra-terrestrial life can be approached as a Search for Extra- Terrestrial Homochirality (SETH). The natural choice for a SETH instrument is optical rotation, and we describe a novel miniaturized space polarimeter, called the SETH Cigar, which could be used to detect optical rotation as the homochiral signature of life on other planets. Moving parts are avoided by replacing the normal rotating polarizer by multiple fixed polarizers at different angles as in the eye of the bee. We believe that homochirality may be found in the subsurface layers on Mars as a relic of extinct life, and on other solar system bodies as a sign of advanced pre-biotic chemistry. We discuss the chiral GC-MS planned for the Roland lander of the Rosetta mission to a comet and conclude with theories of the physical origin of homochirality.

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