Regio- and diastereo-selectivity of montmorillonite-catalyzed oligomerization of racemic adenosine 5′-phosphorimidazolide

Nucleosides, Nucleotides and Nucleic Acids

Volumn 27, Issue 4, 2008, Pages 421-430

  Urata, Hidehito ^a   Fujimori, Mami ^a   Aono, Chie ^a   Yamakawa, Tomomi ^a   Harada, Emi ^a   Akagi, Masao ^a  

^a OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

Clay catalyzed oligomerization; Cyclic nucleotide; Mononucleotide; Racemate; RNA

Indexed keywords

ADENOSINE 5' PHOSPHORIMIDAZOLIDE; DIMER; IMIDAZOLE DERIVATIVE; MONTMORILLONITE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; CYCLIZATION; DIMERIZATION; ENZYMATIC DEGRADATION; OLIGOMERIZATION; STEREOCHEMISTRY;

ADENOSINE MONOPHOSPHATE; ALUMINUM SILICATES; BENTONITE; CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIMERIZATION; ENDORIBONUCLEASES; IMIDAZOLES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 42049085136     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770801954955     Document Type: Article

References (21)

1. Mason, S.F. Origins of biomolecular handedness. Nature 1984, 311, 19-23.
2. Negi, S.; Dhanasekaran, M.; Hirata, T.; Urata, H.; Sugiura, Y. Biomolecular mirror-image recognition: reciprocal chiral-specific DNA binding of synthetic enantiomers of zinc finger domain from GAGA factor. Chirality 2006, 18, 254-258.
3. Milton, R.C.; Milton, S.C.; Kent, S.B. Total chemical synthesis of a D-enzyme: the enantiomers of HIV-1 protease show reciprocal chiral substrate specificity. Science 1992, 256, 1445-1448.
4. Cech, T.R.; Zaug, A.J.; Grabowski, P.J. In vitro splicing of the ribosomal RNA precursor of Tetrahymena: involvement of a guanosine nucleotide in the excision of the intervening sequence. Cell 1981, 27, 487-496.
5. Kruger, K.; Grabowski, P.J.; Zaug, A.J.; Sands, J.; Gottschling, D.E.; Cech, T.R. Self-splicing RNA: autoexcision and autocyclization of the ribosomal RNA intervening sequence of Tetrahymena. Cell 1982, 31, 147-157.
6. Gesteland, R.F.; Atkins, J.F. The RNA World. Cold Spring Harbor Lab. Press: New York, 1993.
7. Bada, J.L. Origins of homochirality. Nature 1995, 374, 594-595.
8. Joyce, G.F.; Inoue, T.; Orgel, L.E. Non-enzymic template-directed synthesis on RNA random copolymers. Poly(C, U) templates. J. Mol. Biol. 1984, 176, 279-306.
9. Joyce, G.F.; Visser, G.M.; van Boeckel, C.A.; van Boom, J.H.; Orgel, L.E.; van Westrenen, J. Chiral selection in poly(C)-directed synthesis of oligo(G). Nature 1984, 310, 602-604.
10. Ferris, J.P.; Ertem, G. Oligomerization of ribonucleotides on montmorillonite: reaction of the 5′-phosphorimidazolide of adenosine. Science 1992, 257, 1387-1389.
11. Ferris, J.P.; Hill, A.R. Jr.; Liu, R.; Orgel, L.E. Synthesis of long prebiotic oligomers on mineral surfaces. Nature 1996, 381, 59-61.
12. Urata, H.; Aono, C.; Ohmoto, N.; Shimamoto, Y.; Kobayashi, Y.; Akagi, M. Efficient and homochiral selective oligomerization of racemic ribonucleotides on mineral surface. Chem. Lett. 2001, 324-325.
13. Joshi, P.C.; Ferris, J.P.; Pitsch, S. Homochiral selection in the montmorillonite-catalyzed and uncatalyzed Prebiotic synthesis of RNA. Chem. Commun. 2000, 2497-2498.
14. Joshi, P.C.; Pitsch, S.; Ferris, J.P. Selectivity of montmorillonite catalyzed prebiotic reactions of D,L-nucleotides. Origins Life Evol. Biospheres 2007, 37, 3-26.
15. Yoshikawa, M.; Kato, T.; Takenishi, T. Phosphorylation. III. Selective phosphorylation of unprotected nucleosides. Bull. Chem. Soc. Jpn. 1969, 42, 3505-3508.
16. Urata, H.; Hara, H.; Hirata, Y.; Ohmoto, N.; Akagi, M. Synthesis and structural characterization of diastereomeric isomers of RNA trimer adenylyl(3′-5′)adenylyl(3′-5′)adenosine. Tetrahedron: Asymmetry 2005, 16, 2908-2917.
17. Urata, H.; Go, M.; Ohmoto, N.; Minoura, K.; Akagi, M. Helical structure of heterochiral RNA dimers: helical sense of ApA is determined by chirality of 3′-end residue. Chem. Commun. 2002, 544-545.
18. Kanavarioti, A. Dimerization in highly concentrated solutions of phosphoimidazolide activated mononucleotides. Origins Life Evol. Biosphere 1997, 27, 357-376.
19. Greer, C.L.; Javor, B.; Abelson, J. RNA ligase in bacteria: formation of a 2′,5′ linkage by an E. coli extract. Cell 1983, 33, 899-906.
20. Urata, H.; Sasaki, R.; Morita, H.; Kusumoto, M.; Ogawa, Y.; Mitsuda, K.; Akagi, M. Kinetic analysis of hydrolytic reaction of homo- and heterochiral adenylyl(3′-5′)adenosine isomers: breaking homochirality reduces hydrolytic stability of RNA. Chem. Commun. 2005, 2578-2580.
21. Osawa, K.; Urata, H.; Sawai, H. Chiral selection in oligoadenylate formation in the presence of a metal ion catalyst or poly(U) template. Origins Life Evol. Biospheres 2005, 35, 213-223.