Absolute configuration of 3‐hydroxy acids formed by Stenotrophomonas maltophilia: Application of multidimensional gas chromatography and circular dichroism spectroscopy

Medientyp: E-Artikel
Titel: Absolute configuration of 3‐hydroxy acids formed by Stenotrophomonas maltophilia: Application of multidimensional gas chromatography and circular dichroism spectroscopy
Beteiligte: Weil, Kerstin; Humpf, Hans‐Ulrich; Schwab, Wilfried; Schreier, Peter
Erschienen: Wiley, 2002
Erschienen in: Chirality
Sprache: Englisch
DOI: 10.1002/chir.10029
ISSN: 0899-0042; 1520-636X
Schlagwörter: Organic Chemistry ; Spectroscopy ; Drug Discovery ; Pharmacology ; Catalysis ; Analytical Chemistry
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Beschreibung: <jats:title>Abstract</jats:title><jats:p>The soil bacterium <jats:italic>Stenotrophomonas maltophilia</jats:italic> was found to transform various long‐chain fatty acids selectively into 3‐hydroxy fatty acids of shorter chain length. Their chiral evaluation was performed by multidimensional gas chromatography (MDGC) on modified cyclodextrin phase comparing the enantiodistribution of 1,3‐diol formed without loss of stereochemical information from a representative microbial product with those of synthetic (3<jats:italic>RS</jats:italic>)‐ and (3<jats:italic>S</jats:italic>)‐1,3‐diols. Enantiomeric excesses of 84–98% (<jats:italic>R</jats:italic>) were determined for the microbially produced 3‐hydroxy acids. In addition, the CD exciton chirality method was applied to determine their absolute configuration. Derivatization with 9‐anthryldiazomethane and 2‐naphthoylimidazole led to the required bichromophoric structures. Their CD spectra displayed a positive first Cotton effect around 254 nm and a negative second Cotton effect around 237 nm, which confirmed the (<jats:italic>R</jats:italic>)‐configuration of the bacterial products. Chirality 14:51–58, 2002. © 2002 Wiley‐Liss, Inc.</jats:p>

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