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1. (Article ID: 4988)
Choma A, Komaniecka I, Zebracki K
Structure, biosynthesis and function of unusual lipids A from nodule-inducing and N2-fixing bacteria
Biochimica et Biophysica Acta 1862(2) (2017)
196-209
This review focuses on the chemistry and structures of (Brady)rhizobium lipids A, indispensable parts of lipopolysaccharides. These lipids contain unusual (omega-1) hydroxylated very long chain fatty acids, which are synthesized by a very limited group of bacteria, besides rhizobia. The significance and requirement of the very long chain fatty acids for outer membrane stability as well as the genetics of the synthesis pathway are discussed. The biological role of these fatty acids for bacterial life in extremely different environments (soil and intracellular space within nodules) is also considered.
lipid A, Rhizobium, Nodule-forming bacteria, Very long chain fatty acids (VLCFA)
NCBI PubMed ID: 27836696Publication DOI: 10.1016/j.bbalip.2016.11.004Journal NLM ID: 0217513Publisher: Elsevier
Correspondence: adam.choma
poczta.umcs.lublin.pl
Institutions: Department of Genetics and Microbiology, Maria Curie-Sklodowska University, Akademicka 19, 20-033 Lublin, Poland
The publication contains the following compound(s):
- Compound ID: 314
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R-3HOMyr-(1-2)-+
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Myr-(1-3)-R-3HOMyr-(1-3)-+ |
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Lau-(1-3)-R-3HOMyr-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
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P-4)-+ |
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R-3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: LPS, lipid A, glycolipid, phosphoglycolipid
- Compound ID: 8740
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3HOPam-(1-2)-+
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a-D-GalpA-(1-4)-+ |
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3HOBut-(1-27)-27HOMon-(1-3)-3HOPam-(1-2)-b-D-GlcpN-(1-6)-GlcN-onic
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3HOMyr-(1-3)-+ |
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3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 12540
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3HOMyr-(1-3)-+ 3HOPam-(1-2)-+
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3HOBut-(1-27)-27HOMon-(1-3)-3HOPam-(1-2)-b-D-GlcpN-(1-6)-a-D-GlcpN-(1-P
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P-4)-+ 3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 2176
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3HOPam-(1-2)-+
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3HOMyr-(1-3)-+ |
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27HOMon-(1-3)-3HOPam-(1-2)-b-D-GlcpN-(1-6)-GlcN-onic
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3HOMyr-(1-3)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 12541
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Ach-(1-3)-3HOiC13-(1-3)-+ 3HOiC13-(1-3)-+
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27HOMon-(1-3)-3HOAch-(1-2)-b-D-GlcpN3N-(1-6)-a-D-GlcpN3N-(1-1)-a-D-GalpA
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P-4)-+ 3HOAch-(1-2)-+ |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 12543
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/Variants 0/-27HOMon-(1-3)-3HOLau-(1-3)-+ 3HOMyr-(1-2)-+
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?%Subst-(34-27)-27HOMon-(1-3)-3HOMyr-(1-2)-b-D-GlcpN3N-(1-6)-a-D-GlcpN3N-(1-1)-a-D-GalpA
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a-D-Manp-(1-6)-a-D-Manp-(1-4)-+ 3HOLau-(1-3)-+
/Variants 0/ is:
Subst-(34-27)-
OR (exclusively)
Subst1-(34-27)-
Subst = 34-carboxyl-bacteriohopane-32,33-diol = SMILES CC(CCC{32}(O){33}C(O){34}C(O)=O)C1C2CC[C@@]3(C)[C@]4(C)CCC5C(C)(C)CCC[C@]5(C)C4CCC3[C@@]2(C)CC1;
Subst1 = 34-carboxyl-2β-methyl-bacteriohopane-32,33-diol = SMILES CC(CCC(O)C(O){34}C(O)=O)C1C2CC[C@@]3(C)[C@]4(C)CCC5C(C)(C)C[C@@H](C)C[C@]5(C)C4CCC3[C@@]2(C)CC1 |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 12545
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LIP-(1-3)-3HOMyr-(1-3)-+
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LIP-(1-3)-Subst-(1-2)-+ |
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LIP-(1-3)-3HOMyr-(1-3)-b-D-GlcpN3N-(1-6)-a-D-GlcpN3N-(1-1)-a-D-GlcpA
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3HOSte-(1-2)-+
Subst = 3-hydroxy-13E-eicosenoic acid = SMILES CCCCCC/C=C/CCCCCCCCC{3}C(O)C{1}C(O)=O |
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Structure type: oligomer
Compound class: lipid A
- Compound ID: 12542
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a-D-Manp-(1-6)-a-D-Manp-(1-4)-+ 3HOMyr-(1-2)-+
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3HOBut-(1-27)-27HOMon-(1-3)-3HOLau-(1-3)-b-D-GlcpN3N-(1-6)-a-D-GlcpN3N-(1-1)-a-D-Manp
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27HOMon-(1-3)-3HOMyr-(1-2)-+ 3HOLau-(1-3)-+ |
Show graphically |
Structure type: oligomer
Compound class: lipid A
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