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A novel sphingophosphonolipid head group 1‐hydroxy‐2‐aminoethyl phosphonate in Bdellovibrio stolpii
Author(s) -
Watanabe Yoko,
Nakajima Masaharu,
Hoshino Tsutomu,
Jayasimhulu Koda,
Brooks Elwood E.,
Kaneshiro Edna S.
Publication year - 2001
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/s11745-001-0751-3
Subject(s) - phosphonate , chemistry , hydrolysis , bacteria , stereochemistry , mass spectrometry , chromatography , biochemistry , biology , genetics
Members of the bacterial genus Bdellovibrio include strains that are free‐living whereas others are known to invade and parasitize larger Gram‐negative bacteria. The bacterium can synthesize several sphingophospholipid compounds including those with phosphoryl bonds as well as phosphonyl bonds. In the present study, the dominant sphingophosphonolipid component was isolated by column chromatography, and the long‐chain bases, fatty acids, and polar head groups were identified by thin‐layer and gas‐liquid chromatographic procedures. The definitive structural identity of the sphingolipid was established by nuclear magnetic resonance and mass spectrometry of hydrolysis products and the intact compound. The compound was identified as N ‐2′‐hydroxypentadecanoyl‐2‐amino‐3,4‐dihydroxyheptadecan‐1‐phosphono‐(1‐hydroxy‐2‐aminoethane).