Abstract
Dehydration/condensation reactions between organic molecules in the prebiotic environment increased the inventory and complexity of organic compounds available for self-assembly into primitive cellular organisms. As a model of such reactions and to demonstrate this principle, we have investigated the esterification reaction between glycerol and decanoic acid that forms glycerol monodecanoate (GMD). This amphiphile enhances robustness of self-assembled membranous structures of carboxylic acids to the potentially disruptive effects of pH, divalent cation binding and osmotic stress. Experimental variables included temperature, water activity and hydrolysis of the resulting ester product, providing insights into the environmental conditions that would favor the formation and stability of this more evolved amphiphile. At temperatures exceeding 50 ∘C, the ester product formed even in the presence of bulk water, suggesting that the reaction occurs at the liquid interface of the two reactants and that the products segregate in the two immiscible layers, thereby reducing hydrolytic back reactions. This implies that esterification reactions were likely to be common in the prebiotic environment as reactants underwent cycles of wetting and drying on rare early landmasses at elevated temperatures
Article PDF
Similar content being viewed by others
References
Apel, C. L., Mautner, M. N. and Deamer, D. W.: 2002, Self-assembled Vesicles of Monocarboxylic Acids and Alcohols: Conditions for Stability and the Encapsulation of Biopolymers, Biochimica et Biophysica Acta 1559, 1–9.
Hanczyc, M. M., Fujikawa, S. M. and Szostak, J. W.: 2003, Experimental Models of Primitive Cellular Compartments: Encapsulation, Growth and Division, Science 302, 618–622.
Hargreaves, W. R., Mulvihill, S. J. and Deamer, D. W.: 1977, Synthesis of Phospholipids and Membranes in Prebiotic Conditions, Nature 266, 78–80.
Huheey, J. E., Keiter, E. A., Keiter, R. L.: 1993, Inorganic Chemistry: Principles of Structure and Reactivity, Harper Collins, New York, NY.
Knauth, L. P.: 2002, Abstract: Life on Land in the Precambian and the Marine vs. Non-Marine Settings of Early Evolution, First Astrobiology Conference at NASA/Ames.
Monnard, P.-A., Apel, C. L., Kanavarioti, A. and Deamer, D. W.: 2002, Influence of Ionic Inorganic Solutes on Self-Assembly and Polymerization Processes Related to Early Forms of Life: Implications for a Prebiotic Aqueous Medium, Astrobiology 2, 139–152.
Palleros, D. R.: 2000, Experimental Organic Chemistry, Wiley, Hoboken, NJ.
Walde, P., Wick, R., Fresta, M., Mangone, A. and Luisi, P. L.: 1994, Autopoietic Self-Reproduction of Fatty Acid Vesicles, J. Am. Chem. Society 116, 11649–11654.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Apel, C.L., Deamer, D.W. The Formation Of Glycerol Monodecanoate By A Dehydration Condensation Reaction: Increasing The Chemical Complexity Of Amphiphiles On The Early Earth. Orig Life Evol Biosph 35, 323–332 (2005). https://doi.org/10.1007/s11084-005-2046-8
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s11084-005-2046-8