Why amino acid stereochemistry always L-configuration

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Discussion Overview

The discussion revolves around the stereochemistry of amino acids, specifically why naturally occurring amino acids predominantly exist in the L-configuration rather than the D-configuration. The scope includes theoretical explanations, potential research references, and implications for protein structure and function.

Discussion Character

  • Exploratory, Technical explanation, Debate/contested

Main Points Raised

  • Some participants inquire about the reasons or theories explaining the predominance of L-configuration amino acids in nature.
  • One participant asserts that D-configuration amino acids do exist, albeit rarely, referencing a Wikipedia article.
  • Another participant mentions various theories and suggests looking into specific research articles for more information.
  • It is noted that the homochirality of amino acids is significant for protein structure, as proteins made from L-amino acids fold uniformly, while those made from a mixture of L and D amino acids may not.
  • A participant questions the implications of using a mixture of L and D amino acids, suggesting that the outcome may depend on the specific context of the mixture.
  • One participant expresses a belief that electromagnetic radiation might play a role in the stereochemical preference, supported by research.

Areas of Agreement / Disagreement

Participants express differing views on the implications of using L and D amino acids in proteins, indicating that there is no consensus on the effects of mixtures of amino acid configurations. The discussion remains unresolved regarding the underlying reasons for the predominance of L-configuration amino acids.

Contextual Notes

Limitations include the lack of definitive proof for the theories mentioned and the dependence on specific definitions of "mixture" when discussing amino acid configurations.

Kglocc
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Any known reasons, research, or theories about why earthly amino-acids exist in the L-configuration and have not been found in D-configuration naturally??
 
Chemistry news on Phys.org
There are many theories. Who knows?

Try these tasty bits for some theories. You need to go to the library to see them, of course.

Nature 389 265 (1997)
Proc. Natl. Acad. Sci. USA 106(14) 5487 (2009)
Angew. Chem. Int. Ed. 38(23) 3418 (1999)
Chem. Rev. 98(7) 2391 (1998)
Mendeleev Commun. 13(3) 129 (2003)
Angew. Chem. Int. Ed. 41(24) 4618 (2002)
 
Most naturally occurring amino acids are L amino acids. Proteins made from L-amino acids are called left-handed proteins. Homochirality of amino acids is important because it ensures uniformity of protein structure. In other words, proteins made of L-amino acids always fold the same way whereas proteins made from a mixture of L and D amino acids would not have the same structure. This is important for many reasons but the most important is probably recognition by enzymes.

I don't know if this is proved or just a theory
 
Moogie said:
In other words, proteins made of L-amino acids always fold the same way whereas proteins made from a mixture of L and D amino acids would not have the same structure.

I think it depends on what you mean by "mixture of L and D amino acids". If you mean mixture in which amino acid is in the form of racemic mixture, and D and L forms are selected at random during peptide synthesis - you are probably right. If you mean mixture containing L and D amino acids, but each given amino acid has always the same conformation - you are probably wrong.

But that's just my guess.
 
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Thanks brains, I appreciate the sources chemisttree.
I checked them all out. I had heard of the meteorite idea. But my gut was telling me that EM radiation must play a role, and now I have proper research to support.
 
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