Evidence map›Paper›PMID 26958372›Full record

ArticleActa crystallographica. Section E, Crystallographic communications2016

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

R W Newberry, R T Raines

Open access · goldAbstract read
In one paragraph

Article in Acta crystallographica. Section E, Crystallographic communications, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

0numbers the graph read from it
0cells of the map it votes in
3citing papers in PubMed
0.5field-weighted citation impact, top 29% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

3 citing papers in PubMed, 6 citations in OpenAlex.

  1. Journal of the American Chemical Society · 2020
    Article
  2. The n→π* Interaction.Accounts of chemical research · 2017
    Article
  3. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

2 authors at 1 institution in 1 country.

R W NewberryDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Ave., Madison, WI, 53706, USA.
R T RainesDepartment 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.
University of Wisconsin–Madison · US

Funding

BIOTECHNOLOGY TRAINING PROGRAMT32GM008349 · NIGMS · UNIVERSITY OF WISCONSIN-MADISON · PI FOX, BRIAN G · 1989 to 2019
$22.5M
COLLAGEN STRUCTURE AND STABILITY IN VITRO AND IN VIVOR01AR044276 · NIAMS · UNIVERSITY OF WISCONSIN-MADISON · PI RAINES, RONALD T · 1996 to 2017
$5.6M
NIAMS NIH HHS R01 AR044276NIGMS NIH HHS T32 GM008349
6 · The paper itself

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.

Indexed as

carbonyl inter­actioncrystal structurehomoserine lactonehydrogen bondingNBO analysis

Identifiers

PMID26958372
PMCPMC4770979
OpenAlexW2239225120

What OpenQuestion holds

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Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.