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Chem Commun (Camb). 2013 Sep 11;49(70):7699-701. doi: 10.1039/c3cc44317e.

n→π* interactions in poly(lactic acid) suggest a role in protein folding.

Author information

1
Department of Chemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706-1322, USA.

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.

PMID:
23897514
PMCID:
PMC3839959
DOI:
10.1039/c3cc44317e
[Indexed for MEDLINE]
Free PMC Article

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