Asymmetric autocatalysis initiated by achiral nucleic acid base adenine: implications on the origin of homochirality of biomolecules

Abstract

Enantiomorphous crystals of adeninium dinitrate acted as the source of chirality in asymmetric autocatalysis producing highly enantioenriched (S)- and (R)-5-pyrimidyl alkanols, with the absolute configurations corresponding to that of crystals.

Enhancement of Intermolecular Magnetic Exchange through Halogen···Halogen Interactions in Bisadeninium Rhenium(IV) Salts

“…The average values of the C-C and C-N bond lengths are in agreement with those found in their corresponding salts. [20][21][22][23][24][25][26]61 As expected, the additional protonation at the N1 and N7 nitrogen atoms makes the bisadeninium cations behave as excellent H-bond donors in 1 (Figures S2 and S4 Overall, the supramolecular packing of 1 and 2 is best described as alternating sheets of bisadeninium cations and [Re IV X6] 2anions developing along the b axis ( Figure 5 and S5). The halide ions are grasped between the nucleobase entities through hydrogen bonds with the nitrogen atoms and lattice water molecules (Figures 3 and 4).…”

“…While there exist paramagnetic compounds with adeninium, all bisadeninium-based salts reported to date are diamagnetic in nature. [20][21][22][23][24][25][26]…”

Impact of the Soai-autocatalysis on natural sciences

“…The chemical content of the papers [1][2][3][4][5][6][7][8][10][11][12][13][14][15][16][17][18][19][20][21][22] from the Soai Research Group from Tokyo University of Science shows that the main goal of scientists cooperating with Kenso Soai is to obtain preparative information about asymmetric autocatalysis. Doubtless, this is the most laborious branch of chemistry and requires a high number of co-workers, reflected by the high number of nodes (135).…”

“…This reaction, now called the Soai reaction [9], is particularly interesting due to its extreme sensitivity [10]. This sensitivity enables the detection of cryptochiral configurations of asymmetric molecules [11], the observation of chiral molecular arrays on the surfaces of crystals of achiral compounds with chiral morphology [12][13][14][15], the structure elucidation of cryptochiral polymers [16], as well as the detection of chirality due to isotope substitution [17][18][19]. The exceptional sensitivity of the Soai reaction enables us to achieve the century-old ambition of preparative chemists: to obtain enantiomeric excesses from achiral-to-chiral reactions without the addition of any chiral auxiliary or application of asymmetric physical fields.…”

Role of Asymmetric Autocatalysis in the Elucidation of Origins of Homochirality of Organic Compounds

“…Symmetry 2019, 11, x FOR PEER REVIEW 9 of Asymmetric autocatalysis initiated by chiral crystals composed of achiral organic compounds.Adenine is another achiral nucleobase. Chiral crystals of adenine dinitrate act as chiral initiators of asymmetric autocatalysis (Scheme 7)[95]. Thus, achiral nucleobases, i.e., cytosine and adenine, can serve as the origin of homochirality in conjunction with asymmetric autocatalysis.…”