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Busset N, Di Lorenzo F, Palmigiano A, Sturiale L, Gressent F, Fardoux J, Gully D, Chaintreuil C, Molinaro A, Silipo A, Giraud E
The Very Long Chain Fatty Acid (C26:25OH) Linked to the Lipid A Is Important for the Fitness of the Photosynthetic Bradyrhizobium Strain ORS278 and the Establishment of a Successful Symbiosis with Aeschynomene Legumes
Frontiers in Microbiology 8 (2017)
1821
|
a-D-Manp-(1-6)-a-D-Manp-(1-4)-+ 3HOMyr-(1-2)-+
| |
Subst-(34-31)-Subst1-(1-3)-3HOLau-(1-3)-b-D-GlcpN3N-(1-6)-a-D-GlcpN3N-(1-1)-a-D-GalpA
| |
LIP25Ac-(1-3)-3HOMyr-(1-2)-+ LIP-(1-3)-+
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 = 2R,31-dihydroxy dotriacontanoic acid = SMILES C{31}C(O)CCCCCCCCCCCCCCCCCCCCCCCCCCCC{2}[C@@H](O){1}C(O)=O |
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Bradyrhizobium sp. ORS 278
(NCBI TaxID 114615,
species name lookup)
Bradyrhizobium BRADO 4680
(Ancestor NCBI TaxID 374,
species name lookup)
Bradyrhizobium sp. BTAi1
(NCBI TaxID 288000,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
The structure was elucidated in this paperNCBI PubMed ID: 28983292Publication DOI: 10.3389/fmicb.2017.01821Journal NLM ID: 101548977Publisher: Lausanne: Frontiers Research Foundation
Correspondence: Eric Giraud <eric.giraud
ird.fr>
Institutions: Institut de Recherche pour le Développement, LSTM, UMR IRD, SupAgro, INRA, Université de Montpellier, CIRADMontpellier, France, Dipartimento di Scienze Chimiche, Complesso Universitario Monte Sant'Angelo, Università di Napoli Federico IINaples, Italy, Istituto per i Polimeri, Compositi e Biomateriali IPCB, Consiglio Nazionale delle RicercheCatania, Italy
In rhizobium strains, the lipid A is modified by the addition of a very long-chain fatty acid (VLCFA) shown to play an important role in rigidification of the outer membrane, thereby facilitating their dual life cycle, outside and inside the plant. In Bradyrhizobium strains, the lipid A is more complex with the presence of at least two VLCFAs, one covalently linked to a hopanoid molecule, but the importance of these modifications is not well-understood. In this study, we identified a cluster of VLCFA genes in the photosynthetic Bradyrhizobium strain ORS278, which nodulates Aeschynomene plants in a Nod factor-independent process. We tried to mutate the different genes of the VLCFA gene cluster to prevent the synthesis of the VLCFAs, but only one mutant in the lpxXL gene encoding an acyltransferase was obtained. Structural analysis of the lipid A showed that LpxXL is involved in the transfer of the C26:25OH VLCFA to the lipid A but not in the one of the C30:29OH VLCFA which harbors the hopanoid molecule. Despite maintaining the second VLCFA, the ability of the mutant to cope with various stresses (low pH, high temperature, high osmolarity, and antimicrobial peptides) and to establish an efficient nitrogen-fixing symbiosis was drastically reduced. In parallel, we investigated whether the BRADO0045 gene, which encodes a putative acyltransferase displaying a weak identity with the apo-lipoprotein N-acyltransferase Lnt, could be involved in the transfer of the C30:29OH VLCFA to the lipid A. Although the mutant exhibited phenotypes similar to the lpxXL mutant, no difference in the lipid A structure was observed from that in the wild-type strain, indicating that this gene is not involved in the modification of lipid A. Our results advance our knowledge of the biosynthesis pathway and the role of VLCFAs-modified lipid A in free-living and symbiotic states of Bradyrhizobium strains.
lipid A, symbiosis, acyltransferase, Bradyrhizobium, Aeschynomene, VLCFA
Structure type: oligomer
Location inside paper: fig.1, fig.3D
Compound class: lipid A
Contained glycoepitopes: IEDB_130701,IEDB_141793,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_983930,SB_198,SB_44,SB_67,SB_72
Methods: PCR, DNA techniques, mild acid hydrolysis, genetic methods, microscopy, statistical analysis, MALDI-MS/MS, cytological analyses, resistance to antibiotics
Comments, role: proposed lipid A structure; 3HOLau and 3HOMyr were substituted at pozitions 3' and 2' of bDGlcpN3N residue by 2,31-dihydroxy dotriacontanoic C32:0 and 25-hydroxy-hexacosanoic C26:0 acids respectively, and LIP at pozition 3 of aGlcpN3N residue was dodec-2-enoic acid - C12:1 C12={2}
Related record ID(s): 12431
NCBI Taxonomy refs (TaxIDs): 114615,
374,
288000
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There is only one chemically distinct structure:
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Busset N, Di Lorenzo F, Palmigiano A, Sturiale L, Gressent F, Fardoux J, Gully D, Chaintreuil C, Molinaro A, Silipo A, Giraud E
The Very Long Chain Fatty Acid (C26:25OH) Linked to the Lipid A Is Important for the Fitness of the Photosynthetic Bradyrhizobium Strain ORS278 and the Establishment of a Successful Symbiosis with Aeschynomene Legumes
Frontiers in Microbiology 8 (2017)
1821
|
a-D-Manp-(1-6)-a-D-Manp-(1-4)-+ 3HOMyr-(1-2)-+
| |
Subst-(34-31)-Subst1-(1-3)-3HOLau-(1-3)-b-D-GlcpN3N-(1-6)-a-D-GlcpN3N-(1-1)-a-D-GalpA
| |
3HOMyr-(1-2)-+ LIP-(1-3)-+
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 = 2R,31-dihydroxy dotriacontanoic acid = SMILES C{31}C(O)CCCCCCCCCCCCCCCCCCCCCCCCCCCC{2}[C@@H](O){1}C(O)=O |
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Bradyrhizobium sp. ORS 278 lpxXL
(Ancestor NCBI TaxID 114615,
species name lookup)
Taxonomic group: bacteria / Proteobacteria
(Phylum: Proteobacteria)
The structure was elucidated in this paperNCBI PubMed ID: 28983292Publication DOI: 10.3389/fmicb.2017.01821Journal NLM ID: 101548977Publisher: Lausanne: Frontiers Research Foundation
Correspondence: Eric Giraud <eric.giraud
ird.fr>
Institutions: Institut de Recherche pour le Développement, LSTM, UMR IRD, SupAgro, INRA, Université de Montpellier, CIRADMontpellier, France, Dipartimento di Scienze Chimiche, Complesso Universitario Monte Sant'Angelo, Università di Napoli Federico IINaples, Italy, Istituto per i Polimeri, Compositi e Biomateriali IPCB, Consiglio Nazionale delle RicercheCatania, Italy
In rhizobium strains, the lipid A is modified by the addition of a very long-chain fatty acid (VLCFA) shown to play an important role in rigidification of the outer membrane, thereby facilitating their dual life cycle, outside and inside the plant. In Bradyrhizobium strains, the lipid A is more complex with the presence of at least two VLCFAs, one covalently linked to a hopanoid molecule, but the importance of these modifications is not well-understood. In this study, we identified a cluster of VLCFA genes in the photosynthetic Bradyrhizobium strain ORS278, which nodulates Aeschynomene plants in a Nod factor-independent process. We tried to mutate the different genes of the VLCFA gene cluster to prevent the synthesis of the VLCFAs, but only one mutant in the lpxXL gene encoding an acyltransferase was obtained. Structural analysis of the lipid A showed that LpxXL is involved in the transfer of the C26:25OH VLCFA to the lipid A but not in the one of the C30:29OH VLCFA which harbors the hopanoid molecule. Despite maintaining the second VLCFA, the ability of the mutant to cope with various stresses (low pH, high temperature, high osmolarity, and antimicrobial peptides) and to establish an efficient nitrogen-fixing symbiosis was drastically reduced. In parallel, we investigated whether the BRADO0045 gene, which encodes a putative acyltransferase displaying a weak identity with the apo-lipoprotein N-acyltransferase Lnt, could be involved in the transfer of the C30:29OH VLCFA to the lipid A. Although the mutant exhibited phenotypes similar to the lpxXL mutant, no difference in the lipid A structure was observed from that in the wild-type strain, indicating that this gene is not involved in the modification of lipid A. Our results advance our knowledge of the biosynthesis pathway and the role of VLCFAs-modified lipid A in free-living and symbiotic states of Bradyrhizobium strains.
lipid A, symbiosis, acyltransferase, Bradyrhizobium, Aeschynomene, VLCFA
Structure type: oligomer
Location inside paper: fig.1, fig.3E
Compound class: lipid A
Contained glycoepitopes: IEDB_130701,IEDB_141793,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_983930,SB_198,SB_44,SB_67,SB_72
Methods: PCR, DNA techniques, mild acid hydrolysis, genetic methods, microscopy, statistical analysis, MALDI-MS/MS, cytological analyses, resistance to antibiotics
Comments, role: proposed lipid A structure of the lpxXL mutant; 3HOLau was substituted at pozition 3'of bDGlcpN3N residue by 2,31-dihydroxy dotriacontanoic C32:0 acid and LIP at pozition 3 of GlcpN3N residue was dodec-2-enoic acid - C12:1 C12={2}
Related record ID(s): 12043
NCBI Taxonomy refs (TaxIDs): 114615
Show glycosyltransferases
There is only one chemically distinct structure:
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