Selectivity of montmorillonite catalyzed prebiotic reactions of D, L-nucleotides.
Identifieur interne : 002B35 ( Main/Exploration ); précédent : 002B34; suivant : 002B36Selectivity of montmorillonite catalyzed prebiotic reactions of D, L-nucleotides.
Auteurs : Prakash C. Joshi [États-Unis] ; Stefan Pitsch ; James P. FerrisSource :
- Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life [ 0169-6149 ] ; 2007.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- MESH :
- chemical , metabolism : Bentonite, Nucleotides.
- chemical : Biopolymers.
- Catalysis, Chromatography, High Pressure Liquid, Mass Spectrometry.
Abstract
The montmorillonite-catalyzed reactions of the 5'-phosphorimidazolides of D, L-adenosine (D, L-ImpA) (Figure 1a. N = A, R = H) and D, L-uridine (Figure 1a., N = U, R = H) yields oligomers that were as long as 7 mers and 6 mers, respectively. The reactions of dilute solutions of D-ImpA and D-ImpU under the same conditions gave oligomers as long as 9 and 8 mers respectively. This demonstrated that oligomer formation is only partially inhibited by incorporation of both the D- and L-enantiomers. The structures of the dimers, trimers and tetramer fractions formed from D, L-ImpA was investigated by selective enzymatic hydrolysis, comparison with authentic samples and mass spectrometry. Homochiral products were present in greater amounts than would be expected if theoretical amounts of each were formed. The ratio of the proportion of homochiral products to that of the amount of each expected for the dimers (cyclic and linear), trimers and tetramers, was 1.3, 1.6, and 2.1, respectively. In the D, L-ImpU reaction homochiral products did not predominate with ratios of dimers (cyclic and linear), trimers and tetramers 0.8, 0.44, and 1.4, respectively. The proportions of cyclic dimers in the dimer fraction were 52-66% with D, L-ImpA and 44-69% with D, L-ImpU. No cyclic dimers were formed in the absence of montmorillonite. The differences in the reaction products of D, L-ImpA and D, L-ImpU are likely to be due to the difference in the orientations of the activated monomers when bound to the catalytic sites on montmorillonite. The consequences of the selectivity of montmorillonite as a prebiotic catalyst are discussed.
DOI: 10.1007/s11084-006-9013-x
PubMed: 17160436
Affiliations:
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Joshi</name><affiliation wicri:level="2"><nlm:affiliation>Department of Chemistry & Chemical Biology and NY Center for Studies on the Origins of Life, Rensselaer Polytechnic Institute, Troy, NY 12180, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry & Chemical Biology and NY Center for Studies on the Origins of Life, Rensselaer Polytechnic Institute, Troy, NY 12180</wicri:regionArea><placeName><region type="state">État de New York</region></placeName></affiliation></author><author><name sortKey="Pitsch, Stefan" sort="Pitsch, Stefan" uniqKey="Pitsch S" first="Stefan" last="Pitsch">Stefan Pitsch</name></author><author><name sortKey="Ferris, James P" sort="Ferris, James P" uniqKey="Ferris J" first="James P" last="Ferris">James P. 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Joshi</name><affiliation wicri:level="2"><nlm:affiliation>Department of Chemistry & Chemical Biology and NY Center for Studies on the Origins of Life, Rensselaer Polytechnic Institute, Troy, NY 12180, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry & Chemical Biology and NY Center for Studies on the Origins of Life, Rensselaer Polytechnic Institute, Troy, NY 12180</wicri:regionArea><placeName><region type="state">État de New York</region></placeName></affiliation></author><author><name sortKey="Pitsch, Stefan" sort="Pitsch, Stefan" uniqKey="Pitsch S" first="Stefan" last="Pitsch">Stefan Pitsch</name></author><author><name sortKey="Ferris, James P" sort="Ferris, James P" uniqKey="Ferris J" first="James P" last="Ferris">James P. Ferris</name></author></analytic><series><title level="j">Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life</title><idno type="ISSN">0169-6149</idno><imprint><date when="2007" type="published">2007</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Bentonite (metabolism)</term><term>Biopolymers</term><term>Catalysis</term><term>Chromatography, High Pressure Liquid</term><term>Mass Spectrometry</term><term>Nucleotides (metabolism)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Bentonite (métabolisme)</term><term>Biopolymères</term><term>Catalyse</term><term>Chromatographie en phase liquide à haute performance</term><term>Nucléotides (métabolisme)</term><term>Spectrométrie de masse</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Bentonite</term><term>Nucleotides</term></keywords><keywords scheme="MESH" type="chemical" xml:lang="en"><term>Biopolymers</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Bentonite</term><term>Nucléotides</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Catalysis</term><term>Chromatography, High Pressure Liquid</term><term>Mass Spectrometry</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Biopolymères</term><term>Catalyse</term><term>Chromatographie en phase liquide à haute performance</term><term>Spectrométrie de masse</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The montmorillonite-catalyzed reactions of the 5'-phosphorimidazolides of D, L-adenosine (D, L-ImpA) (Figure 1a. N = A, R = H) and D, L-uridine (Figure 1a., N = U, R = H) yields oligomers that were as long as 7 mers and 6 mers, respectively. The reactions of dilute solutions of D-ImpA and D-ImpU under the same conditions gave oligomers as long as 9 and 8 mers respectively. This demonstrated that oligomer formation is only partially inhibited by incorporation of both the D- and L-enantiomers. The structures of the dimers, trimers and tetramer fractions formed from D, L-ImpA was investigated by selective enzymatic hydrolysis, comparison with authentic samples and mass spectrometry. Homochiral products were present in greater amounts than would be expected if theoretical amounts of each were formed. The ratio of the proportion of homochiral products to that of the amount of each expected for the dimers (cyclic and linear), trimers and tetramers, was 1.3, 1.6, and 2.1, respectively. In the D, L-ImpU reaction homochiral products did not predominate with ratios of dimers (cyclic and linear), trimers and tetramers 0.8, 0.44, and 1.4, respectively. The proportions of cyclic dimers in the dimer fraction were 52-66% with D, L-ImpA and 44-69% with D, L-ImpU. No cyclic dimers were formed in the absence of montmorillonite. The differences in the reaction products of D, L-ImpA and D, L-ImpU are likely to be due to the difference in the orientations of the activated monomers when bound to the catalytic sites on montmorillonite. The consequences of the selectivity of montmorillonite as a prebiotic catalyst are discussed.</div></front></TEI><affiliations><list><country><li>États-Unis</li></country><region><li>État de New York</li></region></list><tree><noCountry><name sortKey="Ferris, James P" sort="Ferris, James P" uniqKey="Ferris J" first="James P" last="Ferris">James P. Ferris</name><name sortKey="Pitsch, Stefan" sort="Pitsch, Stefan" uniqKey="Pitsch S" first="Stefan" last="Pitsch">Stefan Pitsch</name></noCountry><country name="États-Unis"><region name="État de New York"><name sortKey="Joshi, Prakash C" sort="Joshi, Prakash C" uniqKey="Joshi P" first="Prakash C" last="Joshi">Prakash C. Joshi</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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