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Absolute configuration of 3‐hydroxy acids formed by Stenotrophomonas maltophilia : Application of multidimensional gas chromatography and circular dichroism spectroscopy
Author(s) -
Weil Kerstin,
Humpf HansUlrich,
Schwab Wilfried,
Schreier Peter
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10029
Subject(s) - chemistry , absolute configuration , circular dichroism , chirality (physics) , derivatization , gas chromatography , stenotrophomonas maltophilia , chromatography , enantiomer , cotton effect , spectroscopy , stereochemistry , organic chemistry , mass spectrometry , bacteria , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark , biology , pseudomonas aeruginosa , genetics
Abstract The soil bacterium Stenotrophomonas maltophilia 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 RS )‐ and (3 S )‐1,3‐diols. Enantiomeric excesses of 84–98% ( R ) 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 ( R )‐configuration of the bacterial products. Chirality 14:51–58, 2002. © 2002 Wiley‐Liss, Inc.