@article{deans_taniguchi_chandrashaker_ptaszek_chambers_soares_lindsey_2016, title={Complexity in structure-directed prebiotic chemistry. Unexpected compositional richness from competing reactants in tetrapyrrole formation}, volume={40}, ISSN={["1369-9261"]}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-84979079544&partnerID=MN8TOARS}, DOI={10.1039/c6nj00543h}, abstractNote={Acyclic reactants afford “partially defective” pyrroles that interfere with chain growth of “normal” pyrroles on the path to tetrapyrrole macrocycles.}, number={7}, journal={NEW JOURNAL OF CHEMISTRY}, publisher={Royal Society of Chemistry (RSC)}, author={Deans, Richard M. and Taniguchi, Masahiko and Chandrashaker, Vanampally and Ptaszek, Marcin and Chambers, Dana R. and Soares, Ana R. M. and Lindsey, Jonathan S.}, year={2016}, month={Jul}, pages={6421–6433} }
 @article{soares_thanaiah_taniguchi_lindsey_2013, title={Aqueous-membrane partitioning of beta-substituted porphyrins encompassing diverse polarity}, volume={37}, number={4}, journal={New Journal of Chemistry}, author={Soares, A. R. M. and Thanaiah, Y. and Taniguchi, M. and Lindsey, J. S.}, year={2013}, pages={1087–1097} }
 @article{soares_anderson_chandrashaker_lindsey_2013, title={Catalytic diversification upon metal scavenging in a prebiotic model for formation of tetrapyrrole macrocycles}, volume={37}, ISSN={["1369-9261"]}, DOI={10.1039/c3nj00498h}, abstractNote={A prebiotic model for the formation of tetrapyrrole macrocycles was examined in aqueous solution containing representative Earth-available metals [Mg(II), Mn(II), Fe(II), Co(II), Ni(II), Cu(II), Zn(II) and Pd(II)]. First, a hydrophilic porphyrin (uroporphyrin I) was found to undergo metalation with all metals examined except Mg(II). Second, a competition experiment among the eight metals with uroporphyrin in limiting quantity afforded preferential metalation with Mn(II), Co(II), Cu(II) and Ni(II). A multicomponent analysis method enabled absorption spectrophotometric detection of 8 distinct uroporphyrins (7 metallo-, 1 free base) in a single mixture. Third, a dione–aminoketone reaction was performed in aqueous solution containing the metals followed by photooxidation in the presence of a quinone. The reaction proceeds through multiple stages: (1) dione–aminoketone condensation to give a pyrrole equipped for self-condensation, (2) tetramerization of the pyrrole and cyclization to give uroporphyrinogens, (3) 6e−/6H+ dehydrogenation (e.g., photooxidation) to give the uroporphyrins, and (4) metalation of the uroporphyrins. The presence versus absence of metals resulted in lower yields, yet Mn(II), Fe(II), Co(II), Cu(II) and Zn(II) each individually gave the corresponding metallouroporphyrin [with trivalent metals observed in three cases: Mn(III), Fe(III), and Co(III)]. Analogous reaction in the presence of all eight metals together gave the free base, Mn(III), and Zn(II) chelates whereas other metal chelates could not be reliably detected by absorption spectroscopy or mass spectrometry. Such metalloporphyrins greatly broaden the accessible redox levels, catalytic avenues, and photochemical features versus those of the free base porphyrins. Taken together, scavenging of metals is expected to increase the functional diversity of tetrapyrroles on early Earth.}, number={9}, journal={NEW JOURNAL OF CHEMISTRY}, author={Soares, Ana R. M. and Anderson, Dana R. and Chandrashaker, Vanampally and Lindsey, Jonathan S.}, year={2013}, pages={2716–2732} }
 @article{soares_taniguchi_chandrashaker_lindsey_2013, title={Expanded combinatorial formation of porphyrin macrocycles in aqueous solution containing vesicles. A prebiotic model}, volume={37}, number={4}, journal={New Journal of Chemistry}, author={Soares, A. R. M. and Taniguchi, M. and Chandrashaker, V. and Lindsey, J. S.}, year={2013}, pages={1073–1086} }
 @article{taniguchi_soares_chandrashaker_lindsey_2012, title={A tandem combinatorial model for the prebiogenesis of diverse tetrapyrrole macrocycles}, volume={36}, number={4}, journal={New Journal of Chemistry}, author={Taniguchi, M. and Soares, A. R. M. and Chandrashaker, V. and Lindsey, J. S.}, year={2012}, pages={1057–1069} }
 @article{soares_taniguchi_chandrashaker_lindsey_2012, title={Primordial oil slick and the formation of hydrophobic tetrapyrrole macrocycles}, volume={12}, url={http://www.scopus.com/inward/record.url?eid=2-s2.0-84868383598&partnerID=MN8TOARS}, DOI={10.1089/ast.2012.0857}, abstractNote={The functional end products of the extant biosynthesis of tetrapyrrole macrocycles in photosynthetic organisms are hydrophobic: chlorophylls and bacteriochlorophylls. A model for the possible prebiogenesis of hydrophobic analogues of nature's photosynthetic pigments was investigated by reaction of acyclic reactants in five media: aqueous solution (pH 7, 60°C, 24 h); aqueous solution containing 0.1 M decanoic acid (which forms a turbid suspension of vesicles); or aqueous solution accompanied by dodecane, mesitylene, or a five-component organic mixture (each of which forms a phase-separated organic layer). The organic mixture was composed of equimolar quantities of decanoic acid, dodecane, mesitylene, naphthalene, and pentyl acetate. The reaction of 1,5-dimethoxy-3-methylpentan-2,4-dione and 1-aminobutan-2-one to give etioporphyrinogens was enhanced in the presence of decanoic acid, affording (following chemical oxidation) etioporphyrins (tetraethyltetramethylporphyrins) in yields of 1.4-10.8% across the concentration range of 3.75-120 mM. The yield of etioporphyrins was greater in the presence of the five-component organic mixture (6.6% at 120 mM) versus that with dodecane or mesitylene (2.1% or 2.9%, respectively). The reaction in aqueous solution with no added oil-slick constituents resulted in phase separation-where the organic reactants themselves form an upper organic layer-and the yield of etioporphyrins was 0.5-2.6%. Analogous reactions leading to uroporphyrins (hydrophilic, eight carboxylic acids) or coproporphyrins (four carboxylic acids) were unaffected by the presence of decanoic acid or dodecane, and all yields were at most ∼2% or ∼8%, respectively. Taken together, the results indicate a facile means for the formation of highly hydrophobic constituents of potential value for prebiotic photosynthesis.}, number={11}, journal={Astrobiology}, publisher={Mary Ann Liebert Inc}, author={Soares, A. R. M. and Taniguchi, M. and Chandrashaker, V. and Lindsey, Jonathan}, year={2012}, pages={1055–1068} }
 @article{soares_taniguchi_chandrashaker_lindsey_2012, title={Self-organization of tetrapyrrole constituents to give a photoactive protocell}, volume={3}, number={6}, journal={Chemical Science}, author={Soares, A. R. M. and Taniguchi, M. and Chandrashaker, V. and Lindsey, J. S.}, year={2012}, pages={1963–1974} }