The problem discussed in this paper is the connection between the unique property of biopolymers (proteins, DNA and RNA), i.e. homochirality, and their main functional property, i.e. self-replication. Our approach is based on an analysis of the conditions for the origination of the mechanism of self-replication of chiral polymers. It is demonstrated that self-replication could originate only on the basis of homochiral structures, possessing stereospecific (enzymatic) activity. It is also shown that complete breaking of the mirror symmetry of the organic medium is required both at the stage of polymeric takeover and at the stage of formation of structures possessing stereospecific activity. This requirement is satisfied only in the framework of the mechanism of spontaneous symmetry breaking i.e. the mechanism of non-equilibrium phase transition from the racemic state of the organic medium to the chirally pure one. The results obtained suggest that homochirality is a necessary condition for the origination of biological specificity and plays a fundamental role in the formation of structures capable of self-replication.
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http://dx.doi.org/10.1016/0303-2647(91)90002-3 | DOI Listing |
J Pestic Sci
November 2024
Graduate School of Agriculture, Ehime University.
The syntheses of stereoisomers of butane, butanediol, γ-butyrolactone, tri-substituted tetrahydrofuran (7,9'-epoxy), furofuran, tetra-substituted tetrahydrofuran (7,7'-epoxy and 7,8'-epoxy-8,7'-neolignan), benzylidene, coumarin, indan, and pyran type lignans were achieved. All the stereoisomers of the butane type lignans showed larvicidal activity and anti-phytopathogenic fungal activity. The γ-butyrolactone lignan showed stereospecific cytotoxicity against insect cells.
View Article and Find Full Text PDFArch Biochem Biophys
January 2025
Department of Biochemistry, University of Missouri, Columbia, Missouri 65211, United States; Department of Chemistry, University of Missouri, Columbia, Missouri 65211, United States. Electronic address:
The mitochondrial flavoenzymes proline dehydrogenase (PRODH) and hydroxyproline dehydrogenase (PRODH2) catalyze the first steps of proline and hydroxyproline catabolism, respectively. The enzymes are targets for chemical probe development because of their roles in cancer cell metabolism (PRODH) and primary hyperoxaluria (PRODH2). Mechanism-based inactivators of PRODH target the FAD by covalently modifying the N5 atom, with N-propargylglycine (NPPG) being the current best-in-class of this type of probe.
View Article and Find Full Text PDFChemphyschem
January 2025
Department of Chemistry, Durgapur Government College, West Bengal, Durgapur, 713214, India.
The relative reactivity and cis/trans selectivity of the intramolecular [3+2] cycloaddition (IM32CA) reactions of nitrile oxide (NO), azide (AZ), nitrile sulfide (NS) and nitrile ylide (NY), leading to functionalized heterocycles are studied within the Molecular Electron Density Theory. The kinetically controlled IM32CA reactions are predicted to be cis stereospecific, while the reaction feasibility follows the order NY>NS>NO>AZ with the respective activation Gibbs free energies of 13.7, 17.
View Article and Find Full Text PDFACS Infect Dis
January 2025
Department of Biochemistry and Molecular Biology, University of Georgia, Athens, Georgia 30602, United States.
Half the world's population is at risk of developing a malaria infection, which is caused by parasites of the genus . Currently, resistance has been identified to all clinically available antimalarials, highlighting an urgent need to develop novel compounds and better understand common mechanisms of resistance. We previously identified a novel tetrahydro-β-carboline compound, PRC1590, which potently kills the malaria parasite.
View Article and Find Full Text PDFBiomolecules
December 2024
Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov St., 32, 119991 Moscow, Russia.
Amino acid analogues with a phosphorus-containing moiety replacing the carboxylic group are promising sources of biologically active compounds. The -phosphinic group, with hydrogen-phosphorus-carbon (H-P-C) bonds and a flattened tetrahedral configuration, is a bioisostere of the carboxylic group. Consequently, amino--phosphinic acids undergo substrate-like enzymatic transformations, leading to new biologically active metabolites.
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