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Volumn 9, Issue 15, 2008, Pages 2386-2387

Potentially prebiotic synthesis of pyrimidine β-D-ribonucleotides by photoanomerization/hydrolysis of α-D-cytidine-2′-phosphate

Author keywords

Nucleotides; Photoanomerization; Photohydrolysis; Prebiotic; RNA

Indexed keywords

CYTIDINE PHOSPHATE; PREBIOTIC AGENT; PYRIMIDINE DERIVATIVE; RIBONUCLEOTIDE;

EID: 54349087352     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200800391     Document Type: Article
Times cited : (27)

References (22)
  • 1
    • 0002622819 scopus 로고    scopus 로고
    • Eds, R. F. Gesteland, T. R. Cech, J. F. Atkins, Cold Spring Harbor Laboratory Press, New York
    • G. F. Joyce, L. E. Orgel in The RNA World (Eds.: R. F. Gesteland, T. R. Cech, J. F. Atkins), Cold Spring Harbor Laboratory Press, New York, 1999, pp. 49-77.
    • (1999) The RNA World , pp. 49-77
    • Joyce, G.F.1    Orgel, L.E.2
  • 3
    • 54349092748 scopus 로고    scopus 로고
    • Although a yield for the specific conversion of 1 to 2 is not given in ref. 2, the yield for the overall conversion of D-ribose to 2 is given as 10 to 20, By using phosphate buffer, and several equivalents of cyanoacetylene, we have found that 2 can be produced from 1 in essentially quantitative yield via an anhydronucleoside intermediate; M.W. Powner, J. D. Sutherland, unpublished results
    • Although a yield for the specific conversion of 1 to 2 is not given in ref. 2, the yield for the overall conversion of D-ribose to 2 is given as 10 to 20%. By using phosphate buffer, and several equivalents of cyanoacetylene, we have found that 2 can be produced from 1 in essentially quantitative yield via an anhydronucleoside intermediate; M.W. Powner, J. D. Sutherland, unpublished results.
  • 4
    • 0023672652 scopus 로고    scopus 로고
    • The unlikely prospects of ribose being synthesized in good yield by the formose reaction of formaldehyde have been reviewed: R. Shapiro, Origins Life Evol. Biospheres 1988, 18, 71
    • The unlikely prospects of ribose being synthesized in good yield by the formose reaction of formaldehyde have been reviewed: R. Shapiro, Origins Life Evol. Biospheres 1988, 18, 71.
  • 5
    • 19944415654 scopus 로고    scopus 로고
    • Ribose can be produced in 19% yield by the aldolization of glycolaldehyde and glyceraldehyde catalyzed by the zinc/proline complex, but as a component of a complex mixture including the tetroses, aldo- and ketohexoses, and the other pentoses: J Kofoed, J.-L. Reymond, T. Darbre, Org. Biomol. Chem. 2005, 3, 1850.
    • Ribose can be produced in 19% yield by the aldolization of glycolaldehyde and glyceraldehyde catalyzed by the zinc/proline complex, but as a component of a complex mixture including the tetroses, aldo- and ketohexoses, and the other pentoses: J Kofoed, J.-L. Reymond, T. Darbre, Org. Biomol. Chem. 2005, 3, 1850.
  • 10
    • 0014403635 scopus 로고    scopus 로고
    • Most forms of phosphate activation result in the conversion of 2′- or 3′-nucleotides to nucleoside-2′,3′-cyclic phosphates - in a prebiotic chemistry context see: R. Lohrmann, L. E. Orgel, Science 1968, 161, 64;
    • Most forms of phosphate activation result in the conversion of 2′- or 3′-nucleotides to nucleoside-2′,3′-cyclic phosphates - in a prebiotic chemistry context see: R. Lohrmann, L. E. Orgel, Science 1968, 161, 64;
  • 14
    • 54349127056 scopus 로고    scopus 로고
    • However, in some rare circumstances there can be other consequences of activation of 2′- or 3′-nucleotides-again in a prebiotic context see: J.-P. Biron, A. L. Parkes, R. Pascal, J. D. Sutherland, Angew. Chem. 2005, 117, 6889;
    • However, in some rare circumstances there can be other consequences of activation of 2′- or 3′-nucleotides-again in a prebiotic context see: J.-P. Biron, A. L. Parkes, R. Pascal, J. D. Sutherland, Angew. Chem. 2005, 117, 6889;
  • 15
    • 27444446594 scopus 로고    scopus 로고
    • However, in some rare circumstances there can be other consequences of activation of 2′- or 3′-nucleotides-again in a prebiotic context see: J.-P. Biron, A. L. Parkes, R. Pascal, J. D. Sutherland, Angew. Chem. Int. Ed. 2005, 44, 6731.
    • However, in some rare circumstances there can be other consequences of activation of 2′- or 3′-nucleotides-again in a prebiotic context see: J.-P. Biron, A. L. Parkes, R. Pascal, J. D. Sutherland, Angew. Chem. Int. Ed. 2005, 44, 6731.
  • 16
    • 33846038278 scopus 로고    scopus 로고
    • α-D-Cytidine-5′-phosphate can be formed in > 30% yield in a two-step process starting from 4 and D-glyceraldehyde-3-phosphate
    • α-D-Cytidine-5′-phosphate can be formed in > 30% yield in a two-step process starting from 4 and D-glyceraldehyde-3-phosphate: C. Anastasi, M. A. Crowe, J. D. Sutherland, J. Am. Chem. Soc. 2007, 129, 24.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 24
    • Anastasi, C.1    Crowe, M.A.2    Sutherland, J.D.3
  • 17
    • 54349093946 scopus 로고    scopus 로고
    • The two minor arabinonucleoticle products 10 were identified after treatment of the reaction mixture with alkaline phosphatase and spiking with α- and β-D-arabinocytidine standards.
    • The two minor arabinonucleoticle products 10 were identified after treatment of the reaction mixture with alkaline phosphatase and spiking with α- and β-D-arabinocytidine standards.
  • 19
    • 34250201455 scopus 로고    scopus 로고
    • A 2′-hydroxyoxacarbenium ion being too unstable to form a discrete intermediate: J. A. B. McCann, P. J. Berti, J. Am. Chem. Soc. 2007, 129, 7055.
    • A 2′-hydroxyoxacarbenium ion being too unstable to form a discrete intermediate: J. A. B. McCann, P. J. Berti, J. Am. Chem. Soc. 2007, 129, 7055.
  • 22
    • 54349125835 scopus 로고    scopus 로고
    • M2 nature of the displacement reaction, purine β-D-ribonucleotides should predominate.
    • M2 nature of the displacement reaction, purine β-D-ribonucleotides should predominate.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.