a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA (PAMDB006295)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB006295
Identification
Name: a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA
Description:alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid IVA is an intermediate in (Kdo)2-lipid A biosynthesis I pathway in E.coli. It is a substrate for the enzyme lauroyl acyltransferase which catalyzes the reaction a dodecanoyl-[acp] + alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-lipid IVA -> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-(lauroyl)-lipid IVA + a holo-[acyl-carrier protein]. It is also a intermediate in superpathway of (Kdo)2-lipid A biosynthesis (BioCyc compound: KDO2-LIPID-IVA) .
Structure
Thumb
Synonyms:Not Available
Chemical Formula: C84H148N2O37P2
Average Molecular Weight: 1840.036
Monoisotopic Molecular Weight: 1838.926909189
InChI Key: XAOLJGCZESYRFT-UHFFFAOYSA-H
InChI:InChI=1S/C84H154N2O37P2/c1-5-9-13-17-21-25-29-33-37-41-55(89)45-65(96)85-69-77(117-67(98)47-57(91)43-39-35-31-27-23-19-15-11-7-3)73(102)63(115-80(69)123-125(110,111)112)53-113-79-70(86-66(97)46-56(90)42-38-34-30-26-22-18-14-10-6-2)78(118-68(99)48-58(92)44-40-36-32-28-24-20-16-12-8-4)76(122-124(107,108)109)64(116-79)54-114-83(81(103)104)50-62(72(101)75(120-83)61(95)52-88)119-84(82(105)106)49-59(93)71(100)74(121-84)60(94)51-87/h55-64,69-80,87-95,100-102H,5-54H2,1-4H3,(H,85,96)(H,86,97)(H,103,104)(H,105,106)(H2,107,108,109)(H2,110,111,112)/p-6
CAS number: Not Available
IUPAC Name:Not Available
Traditional IUPAC Name: Not Available
SMILES:CCCCCCCCCCCC(O)CC(=O)NC1C(OP([O-])([O-])=O)OC(COC2OC(COC3(CC(OC4(CC(O)C(O)C(O4)C(O)CO)C([O-])=O)C(O)C(O3)C(O)CO)C([O-])=O)C(OP([O-])([O-])=O)C(OC(=O)CC(O)CCCCCCCCCCC)C2NC(=O)CC(O)CCCCCCCCCCC)C(O)C1OC(=O)CC(O)CCCCCCCCCCC
Chemical Taxonomy
Taxonomy DescriptionNot Available
Kingdom Not Available
Super ClassNot Available
Class Not Available
Sub ClassNot Available
Direct Parent Not Available
Alternative Parents Not Available
Substituents Not Available
Molecular Framework Not Available
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:Not Available
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
alpha-Kdo-(2??)-lipid IVA + CMP-3-Deoxy-D-manno-octulosonate > Cytidine monophosphate + Hydrogen ion + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + Cytidine monophosphate + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA
a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + dodecanoyl-[acp]? + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA > Lauroyl-KDO2-lipid IV(A) + a holo-[acyl-carrier protein]
a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + PE(12:0/10:0) + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA > 1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + phosphoethanolamine-Kdo2-lipid A + Phosphoethanolamine KDO(2)-lipid (A)
PE(16:0/16:0) + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA > phosphoethanolamine-Kdo2-lipid A + 1,2-dihexadecanoyl-rac-glycerol + Phosphoethanolamine KDO(2)-lipid (A)
a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + a palmitoleoyl-[acp]? > KDO2-(palmitoleoyl)-lipid IVA + a holo-[acyl-carrier protein]
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 Pw000831Pw000831 greyscalePw000831 simple
lipopolysaccharide biosynthesis IIPW001905 Pw001905Pw001905 greyscalePw001905 simple
lipopolysaccharide biosynthesis IIIPW002059 Pw002059Pw002059 greyscalePw002059 simple
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
alpha-Kdo-(2??)-lipid IVA + CMP-3-Deoxy-D-manno-octulosonate > Cytidine monophosphate + Hydrogen ion + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + Cytidine monophosphate + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA
a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + dodecanoyl-[acp]? + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA > Lauroyl-KDO2-lipid IV(A) + a holo-[acyl-carrier protein]
a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + PE(12:0/10:0) + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA > 1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + phosphoethanolamine-Kdo2-lipid A + Phosphoethanolamine KDO(2)-lipid (A)
PE(16:0/16:0) + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA + a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA > phosphoethanolamine-Kdo2-lipid A + 1,2-dihexadecanoyl-rac-glycerol + Phosphoethanolamine KDO(2)-lipid (A)
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-0000000090-8a7d9022617b80a2b875View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-1100000090-797c4db9457d87df826dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9340000120-1461aa4efbef7d039b61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000f-3030000090-3112b8ef03d5d44a7b3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ukc-9742000030-785ce5d9cbacbe538508View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06xx-9551000000-d01bd711c23f6a8317c5View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink

Enzymes

Protein Details
• 3-deoxy-D-manno-octulosonic-acid transferase
General function:
Involved in biosynthetic process
Specific function:
Essential step in lipopolysaccharides biosynthesis. Acts at transfer of 3-deoxy-D-mono octulonic acid (KDO) from CMP-KDO to a tetraacyldisaccharide 1,4'-bisphosphate precursor of lipid A (lipid IVA). Transfers two molecules of KDO to lipid IVA. Degraded by FtsH; therefore FtsH regulates the addition of the sugar moiety of the LPS and thus the maturation of the LPS precursor
Gene Name:
waaA
Locus Tag:
PA4988
Molecular weight:
46.5 kDa