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Oligomerization of 3′-amino-3′-deoxyguanosine-5′-phosphorimidazolidate on a d(CpCpCpCpC) template

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Summary

3′-Amino-3′-deoxyguanosine-5′-phosphorimidazolidate (ImpGnh 2) oligomerizes more rapidly and regiospecifically than related nucleotide derivatives on a d(CpCpCpCpC) template. The greater nucleophilicity of the amino group leads to efficient oligomerization even when the structure of the double-helical complex formed by the template and the substrate is not optimal for reaction. The use of amine-containing analogues should permit us to develop models of potentially prebiotic polymerization reactions that cannot be studied easily using natural nucleotides.

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Abbreviations

pG:

guanosine-5′-phosphate

pGnh 2 :

3′-amino-3′-deoxyguanosine-5′-phosphate

2-MeImpG:

guanosine-5′-phosphoro-(2-methyl)-imidazolidate

ImpGnh 2 :

3′-amino-3′-deoxyguanosine-5′-phosphorimidazolidate

d(CpCpCpCpC):

pentadeoxycytidine tetraphosphate

d(pC)5 :

pentadeoxycytidylic acid

(pG)i (i=2, 3,...):

oligomers of pG

(pGnh)ipGnh 2 (i=2, 3, ...):

oligomers of pGnh 2 having exclusively (3′–5′) phosphor-amidate linkages

poly(C):

polycytidylate

poly(dC):

polydeoxycytidylate

HPLC:

high performance liquid chromatography

References

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Authors and Affiliations

  1. The Salk Institute for Biological Studies, PO Box 85800, 92138, San Diego, California, USA

    Mahrokh Tohidi, Wojciech S. Zielinski & Leslie E. Orgel

  2. Molecular Biology Institute, University of California, Los Angeles, 405 Hilgard Avenue, 90024, Los Angeles, California, USA

    C. -H. Betty Chen

Authors
  1. Mahrokh Tohidi
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  2. Wojciech S. Zielinski
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  3. C. -H. Betty Chen
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  4. Leslie E. Orgel
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Tohidi, M., Zielinski, W.S., Chen, C.H.B. et al. Oligomerization of 3′-amino-3′-deoxyguanosine-5′-phosphorimidazolidate on a d(CpCpCpCpC) template. J Mol Evol 25, 97–99 (1987). https://doi.org/10.1007/BF02101750

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  • DOI: https://doi.org/10.1007/BF02101750

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