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Acta Crystallogr E Crystallogr Commun. 2016 Jan 9;72(Pt 2):136-9. doi: 10.1107/S2056989015024913. eCollection 2016 Feb 1.

Crystal structure of N-(3-oxo-butano-yl)-l-homoserine lactone.

Author information

1
Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave., Madison, WI, 53706, USA.
2
Department of Chemistry, University of Wisconsin-Madison, 1101 University Ave., Madison, WI, 53706, USA; Department of Biochemistry, University of Wisconsin-Madison, 433 Babcock Dr., Madison, WI, 53706, USA.

Abstract

The structure and absolute configuration of the title compound, C8H11NO4, which is a known quorum-sensing modulator, have been determined. The mol-ecule exhibits signs of an intra-molecular attractive carbon-yl-carbonyl n→π* inter-action between the amide and lactone ester groups, specifically - a short contact of 2.709 (2) Å between the amide oxygen atom and ester carbon atom, approach of the amide oxygen atom to the ester carbonyl group along the Bürgi-Dunitz trajectory, at 99.1 (1)°, and pyramidalization of the ester carbonyl group by 1.1 (1)°. Moreover, a similar n→π* inter-action is observed for the amide carbonyl group approached by the ketone oxygen donor. These inter-actions apparently affect the conformation of the uncomplexed mol-ecule, which adopts a different shape when bound to protein receptors. In the crystal, the mol-ecules form translational chains along the a axis via N-H⋯O hydrogen bonds.

KEYWORDS:

NBO analysis; carbonyl inter­action; crystal structure; homoserine lactone; hydrogen bonding

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