KDO2-Lipid A (ECMDB21031) (M2MDB001447)
Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 2.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 14:55:18 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 17:20:27 -0600 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | KDO2-Lipid A | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | KDO2-Lipid A is an intermediate in the synthesis of LPS. It has two 3-deoxy-D-manno-octulosonic acid (KDO) sugar residues in place of the core, and has no O-antigen. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C110H202N2O39P2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 2238.7184 Monoisotopic: 2237.335997756 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | DIXUKJUHGLIZGU-ZKUMOPDFSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C110H202N2O39P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-92(123)142-82(66-60-54-48-42-35-29-23-17-11-5)72-94(125)146-104-96(112-90(121)71-81(65-59-53-47-41-34-28-22-16-10-4)141-91(122)67-61-55-49-43-36-30-24-18-12-6)105(144-88(102(104)150-152(133,134)135)78-140-109(107(129)130)74-86(98(127)101(148-109)85(119)76-114)147-110(108(131)132)73-83(117)97(126)100(149-110)84(118)75-113)139-77-87-99(128)103(145-93(124)70-80(116)64-58-52-46-40-33-27-21-15-9-3)95(106(143-87)151-153(136,137)138)111-89(120)69-79(115)63-57-51-45-39-32-26-20-14-8-2/h79-88,95-106,113-119,126-128H,7-78H2,1-6H3,(H,111,120)(H,112,121)(H,129,130)(H,131,132)(H2,133,134,135)(H2,136,137,138)/t79?,80?,81?,82?,83-,84-,85-,86-,87-,88-,95-,96-,97-,98-,99-,100-,101-,102-,103-,104-,105-,106-,109-,110-/m1/s1 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | (2R,4R,5R,6R)-4-{[(2R,4R,5R,6R)-2-carboxy-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-5-[(1,3-dihydroxytetradecylidene)amino]-3-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonooxy)oxan-2-yl]methoxy}-5-{[3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-3-(phosphonooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-5-hydroxyoxane-2-carboxylic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | (2R,4R,5R,6R)-4-{[(2R,4R,5R,6R)-2-carboxy-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxan-2-yl]oxy}-6-[(1R)-1,2-dihydroxyethyl]-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-5-[(1,3-dihydroxytetradecylidene)amino]-3-hydroxy-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonooxy)oxan-2-yl]methoxy}-5-{[3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-3-(phosphonooxy)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-5-hydroxyoxane-2-carboxylic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | [H]C(O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO[C@]2([H])O[C@]([H])(CO[C@@]3(C[C@@]([H])(O[C@@]4(C[C@@]([H])(O)[C@@]([H])(O)[C@]([H])(O4)[C@]([H])(O)CO)C(O)=O)[C@@]([H])(O)[C@]([H])(O3)[C@]([H])(O)CO)C(O)=O)[C@@]([H])(OP(O)(O)=O)[C@]([H])(OC(=O)CC([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@]2([H])N=C(O)CC([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)O[C@]([H])(OP(O)(O)=O)[C@]1([H])N=C(O)CC([H])(O)CCCCCCCCCCC | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Lipids and lipid-like molecules | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Glycerophospholipids | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Glycerophosphoglycerols | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Phosphatidylglycerols | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -5 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Membrane | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Adenosine triphosphate + Water + KDO2-Lipid A > ADP + Hydrogen ion + Phosphate + KDO2-Lipid A Adenosine triphosphate + Water + KDO2-Lipid A > ADP + Hydrogen ion + Phosphate + KDO2-Lipid A Hydrogen ion + Palmitic acid + KDO2-Lipid A > Water + Hepta-acylated KDO2-lipid A Adenosine triphosphate + Water + KDO2-Lipid A > ADP + Hydrogen ion + Phosphate + KDO2-Lipid A Adenosine triphosphate + Water + KDO2-Lipid A > ADP + Hydrogen ion + Phosphate + KDO2-Lipid A KDO(2)-lipid IV(A) with laurate + Myristoyl-ACP (n-C14:0ACP) > acyl carrier protein + KDO2-Lipid A KDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Phosphoethanolamine KDO(2)-lipid (A) KDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) + Phosphoethanolamine KDO(2)-lipid (A) ADP-L-Glycero-D-manno-heptose + KDO2-Lipid A > ADP + Hydrogen ion + heptosyl-kdo2-lipidA KDO2-Lipid A + Acyl-carrier protein + Tetradecanoyl-[acp] + Lauroyl-KDO2-lipid IV(A) <> Tetradecanoyl-[acp] + Lauroyl-KDO2-lipid IV(A) + Acyl-carrier protein a phospholipid + KDO2-Lipid A > a glycerol ester + Hepta-acylated KDO2-lipid A KDO2-Lipid A + 4-amino-4-deoxy-α-L-arabinopyranosyl <i>ditrans,octacis</i>-undecaprenyl phosphate > L-Ara4N-modified KDO2-Lipid A + Di-trans,poly-cis-undecaprenyl phosphate Hydrogen ion + KDO2-Lipid A + ADP-L-Glycero-D-manno-heptose > Heptosyl-KDO2-lipid A + ADP undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose + KDO2-Lipid A + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + Di-trans,poly-cis-undecaprenyl phosphate + Lipid IIA undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose + KDO2-Lipid A + 2 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid A + Di-trans,poly-cis-undecaprenyl phosphate + Lipid IIA | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMPDB Pathways: |
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KEGG Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: |
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References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Links | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in transferase activity, transferring acyl groups
- Specific function:
- Transfers myristate or laurate, activated on ACP, to the lipid IVA moiety of (KDO)2-(lauroyl)-lipid IVA. Decanoyl, palmitoyl, palmitoleoyl, and (R)-3-hydroxymyristoyl-ACP are poor acyl donors. Functions optimally after laurate incorporation by htrB has taken place. Acylates (KDO)2-(lauroyl)-lipid IVA about 100 times faster than (KDO)2-lipid IVA. Displays a preference for myristoyl-ACP over lauroyl-ACP
- Gene Name:
- msbB
- Uniprot ID:
- P24205
- Molecular weight:
- 37410
- General function:
- Involved in catalytic activity
- Specific function:
- Catalyzes the addition of a phosphoethanolamine (pEtN) moiety to the outer 3-deoxy-D-manno-octulosonic acid (KDO) residue of a KDO(2)-lipid A. Phosphatidylethanolamines with one unsaturated acyl group functions as pEtN donors and the reaction releases diacylglycerol
- Gene Name:
- eptB
- Uniprot ID:
- P37661
- Molecular weight:
- 63804
- General function:
- Involved in transferase activity, transferring pentosyl groups
- Specific function:
- Catalyzes the transfer of the L-Ara4N moiety of the glycolipid undecaprenyl phosphate-alpha-L-Ara4N to lipid A. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
- Gene Name:
- arnT
- Uniprot ID:
- P76473
- Molecular weight:
- 62542
Reactions
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate + lipid IV(A) = lipid II(A) + di-trans,octa-cis-undecaprenyl phosphate. |
- General function:
- Involved in transferase activity, transferring glycosyl groups
- Specific function:
- Heptose transfer to the lipopolysaccharide core. It transfers the innnermost heptose to [4'-P](3-deoxy-D-manno- octulosonic acid)2-IVA
- Gene Name:
- rfaC
- Uniprot ID:
- P24173
- Molecular weight:
- 35544
- General function:
- Involved in lipopolysaccharide transport
- Specific function:
- Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
- Gene Name:
- lptG
- Uniprot ID:
- P0ADC6
- Molecular weight:
- 39618
- General function:
- Involved in lipopolysaccharide-transporting ATPase acti
- Specific function:
- Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
- Gene Name:
- lptF
- Uniprot ID:
- P0AF98
- Molecular weight:
- 40357
- General function:
- Involved in nucleotide binding
- Specific function:
- Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
- Gene Name:
- msbA
- Uniprot ID:
- P60752
- Molecular weight:
- 64460
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane. Probably responsible for energy coupling to the transport system
- Gene Name:
- lptB
- Uniprot ID:
- P0A9V1
- Molecular weight:
- 26800
- General function:
- Not Available
- Specific function:
- Not known; overproduction leads to camphor resistance and chromosome condensation
- Gene Name:
- crcA
- Uniprot ID:
- P37001
- Molecular weight:
- 21770
- General function:
- Involved in lipopolysaccharide transmembrane transporter activity
- Specific function:
- Required for the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
- Gene Name:
- lptC
- Uniprot ID:
- P0ADV9
- Molecular weight:
- 21703
- General function:
- Involved in lipopolysaccharide binding
- Specific function:
- Required for the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane. May act as a chaperone that facilitates LPS transfer across the aquaeous environment of the periplasm. Interacts specifically with the lipid A domain of LPS
- Gene Name:
- lptA
- Uniprot ID:
- P0ADV1
- Molecular weight:
- 20127
Transporters
- General function:
- Involved in lipopolysaccharide transport
- Specific function:
- Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
- Gene Name:
- lptG
- Uniprot ID:
- P0ADC6
- Molecular weight:
- 39618
- General function:
- Involved in lipopolysaccharide-transporting ATPase acti
- Specific function:
- Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
- Gene Name:
- lptF
- Uniprot ID:
- P0AF98
- Molecular weight:
- 40357
- General function:
- Involved in nucleotide binding
- Specific function:
- Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
- Gene Name:
- msbA
- Uniprot ID:
- P60752
- Molecular weight:
- 64460