title: Absolute Stereochemistry of 1,2-Diols from Lipids of Thermomicrobia.
abstract: 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.
authors.affiliation: Callaghan Innovation, 69 Gracefield Road, PO Box 31310, Lower Hutt, 5040, New Zealand. Kirill.Lagutin@callaghaninnovation.govt.nz.
authors.forename: Kirill
authors.initials: K
authors.lastname: Lagutin
authors.affiliation: Callaghan Innovation, 69 Gracefield Road, PO Box 31310, Lower Hutt, 5040, New Zealand.
authors.forename: Herbert
authors.initials: H
authors.lastname: Wong
authors.affiliation: Callaghan Innovation, 69 Gracefield Road, PO Box 31310, Lower Hutt, 5040, New Zealand.
authors.forename: Mikhail
authors.initials: M
authors.lastname: Vyssotski
authors.affiliation: Callaghan Innovation, 69 Gracefield Road, PO Box 31310, Lower Hutt, 5040, New Zealand.
authors.forename: Andrew
authors.initials: A
authors.lastname: MacKenzie
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D041862:Chloroflexi / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010743:Phospholipids / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D010743:Phospholipids
keywords: 1,2-Diols; Chiral derivatizing agents; Fatty diols; Thermomicrobia; α-Methoxyphenylacetic acid