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Absolute Stereochemistry of 1,2‐Diols from Lipids of Thermomicrobia
Author(s) -
Lagutin Kirill,
Wong Herbert,
Vyssotski Mikhail,
MacKenzie Andrew
Publication year - 2016
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-016-4124-2
Subject(s) - chemistry , moiety , stereochemistry , glyceride , diol , nuclear magnetic resonance spectroscopy , absolute configuration , derivative (finance) , organic chemistry , fatty acid , financial economics , economics
1,2‐Diol based phospholipids are a well‐known feature of bacteria from the class Thermomicrobia . Since these bacteria contain only lipids with an alkyldiol‐ 1 ‐phosphate backbone instead of sn ‐glycero‐3‐phosphate, it is important to elucidate the stereochemistry of the 1,2‐diols. We have studied the absolute stereochemistry of long‐chain 1,2‐diols isolated from Thermorudis pharmacophila (formerly known as Thermomicrobia sp. WKT50.2) by nuclear magnetic resonance (NMR) using α‐methoxyphenylacetic acid (MPA). Low‐temperature (−60 °C) NMR of bis‐( R )‐MPA ester showed ( R ) stereochemistry of the 1,2‐diols. This is the first report concerning the stereochemistry of natural 1,2‐diols, which replace the glyceride moiety in phospholipids. The ( R ) stereochemistry of the diols is expected as it is the same configuration as for the common bacterial lipid backbone— sn ‐glycero‐3‐phosphate. This is the first application of low‐temperature NMR of a single MPA derivative for assignment of stereochemistry of natural 1,2‐diols. The results were confirmed by the comparison of NMR data with bis‐( R )‐MPA ester of ( R ) and rac‐ 1,2‐octanediol.