Non-Enzymatic Oligomerization of 3', 5' Cyclic AMP

PLoS One. 2016 Nov 1;11(11):e0165723. doi: 10.1371/journal.pone.0165723. eCollection 2016.

Abstract

Recent studies illustrate that short oligonucleotide sequences can be easily produced from nucleotide precursors in a template-free non-enzymatic way under dehydrating conditions, i.e. using essentially dry materials. Here we report that 3',5' cyclic AMP may also serve as a substrate of the reaction, which proceeds under moderate conditions yet with a lower efficiency than the previously reported oligomerization of 3',5' cyclic GMP. Optimally the oligomerization requires (i) a temperature of 80°C, (ii) a neutral to alkaline environment and (iii) a time on the order of weeks. Differences in the yield and required reaction conditions of the oligomerizations utilizing 3',5' cGMP and cAMP are discussed in terms of the crystal structures of the compounds. Polymerization of 3',5' cyclic nucleotides, whose paramount relevance in a prebiotic chemistry context has been widely accepted for decades, supports the possibility that the origin of extant genetic materials might have followed a direct uninterrupted path since its very beginning, starting from non-elaborately pre-activated monomer compounds and simple reactions.

MeSH terms

  • Cyclic GMP / chemistry*
  • Hydrogen-Ion Concentration
  • Kinetics
  • Polymerization*

Substances

  • Cyclic GMP

Grants and funding

This work is supported by the Italian Space Agency (ASI) project “Esobiologia e Ambienti estremi: dalla chimica delle Molecola alla Biologia degli estremofili” Number 2014-026-R.0 (CUP: F 92I14000030005); by the Ministry of Education, Youth and Sports of the Czech Republic under the project CEITEC 2020 (LQ1601); and by the Grant Agency of the Czech Republic, grant number 14-12010S. The MS part of work was carried out with the support of Proteomics Core Facility of CEITEC under CIISB project, ID number LM2015043, funded by the Ministry of Education, Youth and Sports of the Czech Republic. OS and ZZ thanks for support of CSF (project P206/12/G151).