| Primordial Oil Slick and the Formation of Hydrophobic Tetrapyrrole Macrocycles. | |
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MedLine Citation:
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PMID: 23095096 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Abstract 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. Key Words: Origin of life-Prebiotic-Oil slick-Porphyrinogen-Porphyrin-Pyrrole-Partition. Astrobiology 12, xxx-xxx. |
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Authors:
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Ana R M Soares; Masahiko Taniguchi; Vanampally Chandrashaker; Jonathan S Lindsey |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-10-24 |
Journal Detail:
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Title: Astrobiology Volume: - ISSN: 1557-8070 ISO Abbreviation: Astrobiology Publication Date: 2012 Oct |
Date Detail:
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Created Date: 2012-10-25 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101088083 Medline TA: Astrobiology Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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Department of Chemistry, North Carolina State University , Raleigh, North Carolina. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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