| Reactivity of Alanylalanine Diastereoisomers in Neutral and Acid Aqueous Solutions: a Versatile Stereoselectivity. | |
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MedLine Citation:
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PMID: 21562847 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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A good comprehension of the reactivity of peptides in aqueous solution is fundamental in prebiotic chemistry, namely for understanding their stability and behavior in primitive oceans. Relying on the stereoselectivity of the involved reactions, there is a huge interest in amino acid derivatives for explaining the spontaneous emergence of homochirality on primitive Earth. The corresponding kinetic and thermodynamic parameters are however still poorly known in the literature. We studied the reactivity of alanylalanine in acidic to neutral conditions as a model system. The hydrolysis into amino acids, the epimerization of the N-terminal residue, and the cyclization into diketopiperazine could be successfully identified and studied. This kinetic investigation highlighted interesting behaviors. Complex mechanisms were observed in very acidic conditions. The relative kinetic stability of the diastereoisomers of the dipeptide is highly dependent of the pH, with the possibility to dynamically destabilize the thermodynamically more stable diastereoisomers. The existence of the cyclization of dipeptides adds complexity to the system. On one hand it brings additional stereoselectivities; on the other hand fast racemization of heterochiral dipeptides is obtained. |
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Authors:
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Raphaël Plasson; Maika Tsuji; Masazumi Kamata; Kouichi Asakura |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2011-5-12 |
Journal Detail:
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Title: Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life Volume: - ISSN: 1573-0875 ISO Abbreviation: - Publication Date: 2011 May |
Date Detail:
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Created Date: 2011-5-12 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 8610391 Medline TA: Orig Life Evol Biosph Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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Department of Applied Chemistry, Faculty of Science and Technology, Keio University, 3-14-1, Hiyoshi, Kohoku-ku, Yokohamashi, 223-8522, Japan, plasson@applc.keio.ac.jp. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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