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Volumn 8, Issue 10, 2007, Pages 1170-1179

On the prebiotic synthesis of ribonucleotides: Photoanomerisation of cytosine nucleosides and nucleotides revisited

Author keywords

Nucleosides; Photoanomerisation; Photochemistry; Prebiotic; RNA

Indexed keywords

CYTIDINE DEAMINASE; NUCLEOTIDE; PREBIOTIC AGENT; RIBONUCLEOTIDE;

EID: 34547555670     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200700098     Document Type: Article
Times cited : (37)

References (31)
  • 2
    • 34547561981 scopus 로고    scopus 로고
    • Specific anomers of a nucleoside X are given the descriptors α- or β- in the form of a prefix. In the case of nucleotides, the site of nucleoside phosphorylation is additionally indicated by a suffix -n′-P, (or X-2′,3′-cP in the case of nucleoside-2′,3′-cyclic phosphates). For the sake of clarity, furanose and pyranose isomers, and 2′-epimers of a nucleoside/nucleotide are given different compound numbers. However, β-D-ribose-2- phosphate, for which the furanose-pyranose isomerisation is rapid in neutral aqueous solution, is given a single number: 49.
    • Specific anomers of a nucleoside X are given the descriptors α- or β- in the form of a prefix. In the case of nucleotides, the site of nucleoside phosphorylation is additionally indicated by a suffix -n′-P, (or X-2′,3′-cP in the case of nucleoside-2′,3′-cyclic phosphates). For the sake of clarity, furanose and pyranose isomers, and 2′-epimers of a nucleoside/nucleotide are given different compound numbers. However, β-D-ribose-2- phosphate, for which the furanose-pyranose isomerisation is rapid in neutral aqueous solution, is given a single number: 49.
  • 4
    • 19944415654 scopus 로고    scopus 로고
    • It has been shown more recently that ribose can be made in 19% yield by the aldolisation of glycolaldehyde and glyceraldehyde catalysed by the zinc-proline complex: J. Kofoed, J.-L. Reymond, T. Darbre, Org. Biomol. Chem. 2005, 3, 1850. However, it is produced as a component of a complex and intractable mixture including the tetroses, aldo- and ketohexoses, and the other pentoses
    • It has been shown more recently that ribose can be made in 19% yield by the aldolisation of glycolaldehyde and glyceraldehyde catalysed by the zinc-proline complex: J. Kofoed, J.-L. Reymond, T. Darbre, Org. Biomol. Chem. 2005, 3, 1850. However, it is produced as a component of a complex and intractable mixture including the tetroses, aldo- and ketohexoses, and the other pentoses.
  • 7
    • 33749038680 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2006, 45, 6176.
    • (2006) Chem. Int. Ed , vol.45 , pp. 6176
    • Angew1
  • 10
    • 0014852887 scopus 로고
    • The phosphorylation of α-2 using cyclic trimetaphosphate and sodium hydroxide has been described: R. Saffhill
    • The phosphorylation of α-2 using cyclic trimetaphosphate and sodium hydroxide has been described: R. Saffhill, J. Org. Chem. 1970, 35, 2881.
    • (1970) J. Org. Chem , vol.35 , pp. 2881
  • 11
    • 0015211212 scopus 로고    scopus 로고
    • The reaction proceeds through α-2-2′,3′-cP and gives α-2-2′-P and α-2-3′-P in high yield, but the strongly alkaline conditions required raise doubts about the prebiotic plausibility of this reaction. Under more credible prebiotic conditions, β-2 is converted to mixtures that contain β-2-2′, 3′-cP (>30% yield after 24 h) and β-2-5′-P (>20% yield after 4 h) as the major phosphorylation products after heating with inorganic phosphate, urea and ammonium salts in the dry state: R. Lohrmann, L E. Orgel, Science 1971, 171, 490.
    • The reaction proceeds through α-2-2′,3′-cP and gives α-2-2′-P and α-2-3′-P in high yield, but the strongly alkaline conditions required raise doubts about the prebiotic plausibility of this reaction. Under more credible prebiotic conditions, β-2 is converted to mixtures that contain β-2-2′, 3′-cP (>30% yield after 24 h) and β-2-5′-P (>20% yield after 4 h) as the major phosphorylation products after heating with inorganic phosphate, urea and ammonium salts in the dry state: R. Lohrmann, L E. Orgel, Science 1971, 171, 490.
  • 12
    • 34547597332 scopus 로고    scopus 로고
    • 2O.
    • 2O.
  • 20
    • 34547597906 scopus 로고    scopus 로고
    • a of the ureas suggests that they would be poor leaving groups at neutral pH.
    • a of the ureas suggests that they would be poor leaving groups at neutral pH.
  • 21
    • 33947469046 scopus 로고    scopus 로고
    • In the case of uridines, the 1,4-addition of water to the conjugated enone system of the uracil moiety has been suggested: S. Y. Wang, J. Am. Chem. Soc. 1958, 80, 6196
    • In the case of uridines, the 1,4-addition of water to the conjugated enone system of the uracil moiety has been suggested: S. Y. Wang, J. Am. Chem. Soc. 1958, 80, 6196.
  • 25
    • 34547582815 scopus 로고    scopus 로고
    • CCDC 636363 (β-19) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac. uk/data_request/cif
    • CCDC 636363 (β-19) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac. uk/data_request/cif


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.