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- Name help_outline archaetidylglycerol Identifier CHEBI:193565 Charge -1 Formula C46H94O8P InChIKeyhelp_outline AFYVWQWWQKSZEV-XOXLRZKWSA-M SMILEShelp_outline P(OC[C@@H](OCC[C@@H](CCC[C@H](C)CCC[C@@H](CCCC(C)C)C)C)COCC[C@@H](CCC[C@H](C)CCC[C@@H](CCCC(C)C)C)C)(=O)(OC[C@@H](CO)O)[O-] 2D coordinates Mol file for the small molecule Search links Involved in 2 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline AH2 Identifier CHEBI:17499 Charge 0 Formula RH2 SMILEShelp_outline *([H])[H] 2D coordinates Mol file for the small molecule Search links Involved in 2,929 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline S-adenosyl-L-methionine Identifier CHEBI:59789 Charge 1 Formula C15H23N6O5S InChIKeyhelp_outline MEFKEPWMEQBLKI-AIRLBKTGSA-O SMILEShelp_outline C[S+](CC[C@H]([NH3+])C([O-])=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c(N)ncnc12 2D coordinates Mol file for the small molecule Search links Involved in 938 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline glycerol dibiphytanyl glycerol tetraether glycerophospholipid Identifier CHEBI:193567 Charge -2 Formula C92H184O16P2 InChIKeyhelp_outline RJWLQKJWQDVESQ-LEWNNOATSA-L SMILEShelp_outline P(OC[C@H]1OCC[C@@H](CCC[C@H](C)CCC[C@@H](CCCC(C)CCC(CCC[C@H](CCC[C@H](CCC[C@H](CCOC[C@H](OCC[C@@H](CCC[C@H](C)CCC[C@@H](CCCC(C)CCC(CCC[C@H](CCC[C@H](CCC[C@H](CCOC1)C)C)C)C)C)C)COP(=O)(OC[C@@H](CO)O)[O-])C)C)C)C)C)C)(=O)(OC[C@@H](CO)O)[O-] 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline 5'-deoxyadenosine Identifier CHEBI:17319 (CAS: 4754-39-6) help_outline Charge 0 Formula C10H13N5O3 InChIKeyhelp_outline XGYIMTFOTBMPFP-KQYNXXCUSA-N SMILEShelp_outline C[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c(N)ncnc12 2D coordinates Mol file for the small molecule Search links Involved in 76 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline L-methionine Identifier CHEBI:57844 Charge 0 Formula C5H11NO2S InChIKeyhelp_outline FFEARJCKVFRZRR-BYPYZUCNSA-N SMILEShelp_outline CSCC[C@H]([NH3+])C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 131 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline A Identifier CHEBI:13193 Charge Formula R SMILEShelp_outline * 2D coordinates Mol file for the small molecule Search links Involved in 3,001 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
- Name help_outline H+ Identifier CHEBI:15378 Charge 1 Formula H InChIKeyhelp_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILEShelp_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,932 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Cross-references
| RHEA:74535 | RHEA:74536 | RHEA:74537 | RHEA:74538 | |
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| Reaction direction help_outline | undefined | left-to-right | right-to-left | bidirectional |
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Related reactions help_outline
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Publications
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Discovery, structure and mechanism of a tetraether lipid synthase.
Lloyd C.T., Iwig D.F., Wang B., Cossu M., Metcalf W.W., Boal A.K., Booker S.J.
Archaea synthesize isoprenoid-based ether-linked membrane lipids, which enable them to withstand extreme environmental conditions, such as high temperatures, high salinity, and low or high pH values<sup>1-5</sup>. In some archaea, such as Methanocaldococcus jannaschii, these lipids are further mod ... >> More
Archaea synthesize isoprenoid-based ether-linked membrane lipids, which enable them to withstand extreme environmental conditions, such as high temperatures, high salinity, and low or high pH values<sup>1-5</sup>. In some archaea, such as Methanocaldococcus jannaschii, these lipids are further modified by forming carbon-carbon bonds between the termini of two lipid tails within one glycerophospholipid to generate the macrocyclic archaeol or forming two carbon-carbon bonds between the termini of two lipid tails from two glycerophospholipids to generate the macrocycle glycerol dibiphytanyl glycerol tetraether (GDGT)<sup>1,2</sup>. GDGT contains two 40-carbon lipid chains (biphytanyl chains) that span both leaflets of the membrane, providing enhanced stability to extreme conditions. How these specialized lipids are formed has puzzled scientists for decades. The reaction necessitates the coupling of two completely inert sp<sup>3</sup>-hybridized carbon centres, which, to our knowledge, has not been observed in nature. Here we show that the gene product of mj0619 from M. jannaschii, which encodes a radical S-adenosylmethionine enzyme, is responsible for biphytanyl chain formation during synthesis of both the macrocyclic archaeol and GDGT membrane lipids<sup>6</sup>. Structures of the enzyme show the presence of four metallocofactors: three [Fe<sub>4</sub>S<sub>4</sub>] clusters and one mononuclear rubredoxin-like iron ion. In vitro mechanistic studies show that Csp<sup>3</sup>-Csp<sup>3</sup> bond formation takes place on fully saturated archaeal lipid substrates and involves an intermediate bond between the substrate carbon and a sulfur of one of the [Fe<sub>4</sub>S<sub>4</sub>] clusters. Our results not only establish the biosynthetic route for tetraether formation but also improve the use of GDGT in GDGT-based paleoclimatology indices<sup>7-10</sup>. << Less
Nature 609:197-203(2022) [PubMed] [EuropePMC]
This publication is cited by 3 other entries.