ArticleChemical communications (Cambridge, England)2013
n→π* interactions in poly(lactic acid) suggest a role in protein folding.
Article in Chemical communications (Cambridge, England), 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Crystallographic and Computational Analysis of Oxyma B Cocrystals with Nitrogen-Containing Coformers: The Relevant Role ofCrystal growth & design · 2025Article
- Computational Investigation of the Structural Properties of Poly(lactic acid) and Its Stereoisomers: Shape, Size, and Flexibility.Macromolecules · 2025Article
- Fluorescence in "Nonfluorescent" Polymers.ACS omega · 2020Review
- Article
- Relative orientation of the carbonyl groups determines the nature of orbital interactions in carbonyl-carbonyl short contacts.Chemical science · 2019Article
- The n→π* Interaction.Accounts of chemical research · 2017Article
- Reciprocal carbonyl-carbonyl interactions in small molecules and proteins.Nature communications · 2017Article
- Crystal structure of N-(3-oxo-butano-yl)-l-homoserine lactone.Acta crystallographica. Section E, Crystallographic communications · 2016Article
- n→π* interactions engender chirality in carbonyl groups.Organic letters · 2014Article
- A key n→π* Interaction in N-acyl homoserine lactones.ACS chemical biology · 2014Article
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Authors and funding
2 authors.
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Abstract
Poly(lactic acid) (PLA) is a versatile synthetic polyester. We noted that this depsipeptide analog of polyalanine has a helical structure that resembles a polyproline II helix. Using natural bond orbital analysis, we find that n→π* interactions between sequential ester carbonyl groups contribute 0.44 kcal mol(-1) per monomer to the conformational stability of PLA helices. We conclude that analogous n→π* interactions could direct the folding of a polypeptide chain into a polyproline II helix prior to the formation of hydrogen bonds between backbone amides.
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