Structure Determination of a Quartet of Novel Tetraether Lipids from Methanobacterium thermoautotrophicum1

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Abstract
The structures of three of the major polar lipids (PNLla, GLla, and PNGL1) of Methanobacterium thermoautotrophicum were elucidated. These lipids are derivatives of dibiphytanyl diglycerol tetraether (C 40 tetraether; the proposed name is caldarchaeol). PNLla is a C 40 tetraether analog of phosphatidylethanolamine (proposed name: caldarchaetidylethanolamine). GLla was identified as β-D-glucopyranosyI-(l-6)-β-D-glucopyranosyl C 40 tetraether (diglucosyl caldarchaeol). PNGL1 has the polar head groups of both PNLla and GLla; one of the free hy-droxyls of this tetraether is esterified with phosphoethanolamine while the other is linked to a glucosylglucose residue with the same structure as that of GLla (proposed name: diglucosyl caldarchaetidylethanolamine). That is, PNLla (amino-phospholipid), GLla (glycolipid), and PNGL1 (aminophosphoglycolipid) form structurally a quartet of lipids with the bare caldarchaeol. We propose a new systematic nomenclature of archaebacterial polar lipids in the “ DISCUSSION, ” because the alternative names are too lengthy and laboratory designations of these lipids are not at all systematic. This nomenclature starts with giving the names archaeol and caldarchaeol to dialkyl diether of glycerol or other polyol and tetraether of glycerol or other polyol and alkyl alcohols, respectively, because these lipids are specific to archaebacteria. Phospholipids with a phosphodiester bond were named as derivatives of archaetidic acid or caldarchaetidic acid (phospho-monoesters of archaeol and caldarchaeol) by analogy with phosphatidic acid.

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