Other
Scientific paper
Oct 2011
adsabs.harvard.edu/cgi-bin/nph-data_query?bibcode=2011oleb...41..413p&link_type=abstract
Origins of Life and Evolution of Biospheres, Volume 41, Issue 5, pp.413-435
Other
Oligopeptide, Diketopiperazine, Kinetics, Homochirality, Aped Model
Scientific paper
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.
Asakura Kouichi
Kamata Masazumi
Plasson Raphael
Tsuji Maika
No associations
LandOfFree
Reactivity of Alanylalanine Diastereoisomers in Neutral and Acid Aqueous Solutions: a Versatile Stereoselectivity does not yet have a rating. At this time, there are no reviews or comments for this scientific paper.
If you have personal experience with Reactivity of Alanylalanine Diastereoisomers in Neutral and Acid Aqueous Solutions: a Versatile Stereoselectivity, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Reactivity of Alanylalanine Diastereoisomers in Neutral and Acid Aqueous Solutions: a Versatile Stereoselectivity will most certainly appreciate the feedback.
Profile ID: LFWR-SCP-O-1672891