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  Absolute Configuration of In Situ Crystallized (+)-γ-Decalactone

Patzer, M., Nöthling, N., Goddard, R., & Lehmann, C. W. (2021). Absolute Configuration of In Situ Crystallized (+)-γ-Decalactone. Chemistry, 3(2), 578-584. doi:10.3390/chemistry3020040.

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 Creators:
Patzer, Michael1, Author              
Nöthling, Nils1, Author              
Goddard, Richard1, Author              
Lehmann, Christian W.1, Author              
Affiliations:
1Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: γ-(+)-decalactone; absolute configuration; in situ cryo-crystallization; flavoring agent; lactone; hydrogen bonding; crystal structure; X-ray crystallography
 Abstract: Knowledge about the absolute configuration of small bioactive organic molecules is essential in pharmaceutical research because enantiomers can exhibit considerably different effects on living organisms. X-ray crystallography enables chemists to determine the absolute configuration of an enantiopure compound due to anomalous dispersion. Here, we present the determination of the absolute configuration of the flavoring agent (+)-γ-decalactone, which is liquid under ambient conditions. Single crystals were grown from the liquid in a glass capillary by in situ cryo-crystallization. Diffraction data collection was performed using Cu-Kα radiation. The absolute configuration was confirmed. The molecule consists of a linear aliphatic non-polar backbone and a polar lactone head. In the solid state, layers of polar and non-polar sections of the molecule alternating along the c-axis of the unit cell are observed. In favorable cases, this method of absolute configuration determination of pure liquid (bioactive) agents or liquid products from asymmetric catalysis is a convenient alternative to conventional methods of absolute structure determination, such as optical rotatory dispersion, vibrational circular dichroism, ultraviolet-visible spectroscopy, use of chiral shift reagents in proton NMR and Coulomb explosion imaging.

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Language(s): eng - English
 Dates: 2021-04-162021-03-302021-04-182021-04-21
 Publication Status: Published online
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.3390/chemistry3020040
 Degree: -

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Title: Chemistry
  Abbreviation : Chemistry
Source Genre: Journal
 Creator(s):
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Publ. Info: Basel, Switzerland : MDPI
Pages: - Volume / Issue: 3 (2) Sequence Number: - Start / End Page: 578 - 584 Identifier: ISSN: 2624-8549
CoNE: https://pure.mpg.de/cone/journals/resource/111076342752076