Document Detail

Primordial oil slick and the formation of hydrophobic tetrapyrrole macrocycles.
MedLine Citation:
PMID:  23095096     Owner:  NLM     Status:  MEDLINE    
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.
Ana R M Soares; Masahiko Taniguchi; Vanampally Chandrashaker; Jonathan S Lindsey
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.     Date:  2012-10-24
Journal Detail:
Title:  Astrobiology     Volume:  12     ISSN:  1557-8070     ISO Abbreviation:  Astrobiology     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-05     Completed Date:  2013-07-05     Revised Date:  2013-11-05    
Medline Journal Info:
Nlm Unique ID:  101088083     Medline TA:  Astrobiology     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1055-68     Citation Subset:  IM    
Department of Chemistry, North Carolina State University , Raleigh, North Carolina 27695, USA.
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MeSH Terms
Hydrogen-Ion Concentration
Hydrophobic and Hydrophilic Interactions
Oils / chemistry*
Porphyrins / chemical synthesis
Tetrapyrroles / chemical synthesis*
Water / chemistry
Reg. No./Substance:
0/Oils; 0/Porphyrins; 0/Solutions; 0/Tetrapyrroles; 7732-18-5/Water

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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