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2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate (M2MDB001545)

Record Information
Version2.0
Creation Date2012-07-30 14:54:40 -0600
Update Date2015-06-03 17:20:43 -0600
Secondary Accession Numbers
  • ECMDB21136
Identification
Name:2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate
Description2,3,2'3'-tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate is a member of the chemical class known as Dihexoses. These are disaccharides containing two hexose carbohydrates. Lipid IV(A) is involved in KDO metabolism. The enzyme is a single polypeptide that catalyzes the transfer of two KDO residues to a tetraacyldisaccharide-1,4'-bisphosphate precursor of lipid A, designated lipid IVA (Belunis, C. (PMID 7499229) E. coli KdtA (EcKdtA) is a bifunctional enzyme that transfers two KDO units from two CMP-KDO molecules to lipid IV(A). (PMID 20394418) The analog, KDO-lipid IVA, functions as an acceptor, but is mannosylated at less than 1% the rate of KDO2-lipid IVA. (PMID 9446588)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphate
  • 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphoric acid
  • 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate
  • 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphoric acid
  • 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphate
  • 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphoric acid
  • 2,3,2'3'-Tetrakis(b-hydroxymyristoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphate
  • 2,3,2'3'-Tetrakis(b-hydroxymyristoyl)-D-glucosaminyl-1,6-b-D-glucosamine 1,4'-bisphosphoric acid
  • 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate
  • 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphoric acid
  • 2,3,2'3'-Tetrakis(β-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphate
  • 2,3,2'3'-Tetrakis(β-hydroxymyristoyl)-D-glucosaminyl-1,6-β-D-glucosamine 1,4'-bisphosphoric acid
  • 2-Deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[(3R)-3-hydroxytetradecanamido]-4-O-phosphono-b-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[(3R)-3-hydroxytetradecanamido]-1-O-phosphono-a-D-glucopyranose
  • 2-Deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[(3R)-3-hydroxytetradecanamido]-4-O-phosphono-beta-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[(3R)-3-hydroxytetradecanamido]-1-O-phosphono-alpha-D-glucopyranose
  • 2-Deoxy-6-O-(2-deoxy-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[(3R)-3-hydroxytetradecanamido]-4-O-phosphono-β-D-glucopyranosyl)-3-O-[(3R)-3-hydroxytetradecanoyl]-2-[(3R)-3-hydroxytetradecanamido]-1-O-phosphono-α-D-glucopyranose
  • Lipid A disaccharide bisphosphate
  • Lipid a disaccharide bisphosphoric acid
  • Lipid IV(A)
  • Lipid IVa
Chemical Formula:C68H130N2O23P2
Weight:Average: 1405.7069
Monoisotopic: 1404.8539615
InChI Key:KVJWZTLXIROHIL-QDORLFPLSA-N
InChI:InChI=1S/C68H130N2O23P2/c1-5-9-13-17-21-25-29-33-37-41-51(72)45-57(76)69-61-65(90-59(78)47-53(74)43-39-35-31-27-23-19-15-11-7-3)63(80)56(89-68(61)93-95(84,85)86)50-87-67-62(70-58(77)46-52(73)42-38-34-30-26-22-18-14-10-6-2)66(64(55(49-71)88-67)92-94(81,82)83)91-60(79)48-54(75)44-40-36-32-28-24-20-16-12-8-4/h51-56,61-68,71-75,80H,5-50H2,1-4H3,(H,69,76)(H,70,77)(H2,81,82,83)(H2,84,85,86)/t51-,52-,53-,54-,55-,56-,61-,62-,63-,64-,65-,66-,67-,68-/m1/s1
CAS number:Not Available
IUPAC Name:{[(2R,3R,4R,5S,6R)-5-hydroxy-6-({[(2R,3R,4R,5S,6R)-6-(hydroxymethyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-5-(phosphonooxy)oxan-2-yl]oxy}methyl)-3-[(3R)-3-hydroxytetradecanamido]-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}phosphonic acid
Traditional IUPAC Name:lipid iva
SMILES:CCCCCCCCCCC[C@@H](O)CC(=O)N[C@H]1[C@@H](OP(O)(O)=O)O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](OP(O)(O)=O)[C@H](OC(=O)C[C@H](O)CCCCCCCCCCC)[C@H]2NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](O)[C@@H]1OC(=O)C[C@H](O)CCCCCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1-acylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1-acylglycerol-3-phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.009 g/LALOGPS
logP5.33ALOGPS
logP12.8ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)0.61ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area393.39 ŲChemAxon
Rotatable Bond Count62ChemAxon
Refractivity357.6 m³·mol⁻¹ChemAxon
Polarizability160.64 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Adenosine triphosphate + 2,3,2',3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1-phosphate > ADP + Hydrogen ion + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate
CMP-3-Deoxy-D-manno-octulosonate + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate > Cytidine monophosphate + Hydrogen ion + KDO-lipid IV(A)
2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate + CMP-3-Deoxy-D-manno-octulosonate + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> KDO-lipid IV(A) + Cytidine monophosphate
4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate + 2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate > lipid II(A) + di-trans,octa-cis-undecaprenyl phosphate
2,3,2'3'-Tetrakis(beta-hydroxymyristoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate + CMP-3-Deoxy-D-manno-octulosonate > alpha-Kdo-(2->6)-lipid IV(A) + Cytidine monophosphate
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:
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-029i-0419000000-605cb82c32daa4726adfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-2936001001-595c04a099b74200efecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01q9-8978100003-4a52c47bfac648279767View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004j-9542103200-839d5cc8476dc47e87c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9231001100-98e03379715375a1ce15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a0ecfeea3dcc8eea4685View in MoNA
References
References:
  • Belunis, C. J., Clementz, T., Carty, S. M., Raetz, C. R. (1995). "Inhibition of lipopolysaccharide biosynthesis and cell growth following inactivation of the kdtA gene in Escherichia coli." J Biol Chem 270:27646-27652. Pubmed: 7499229
  • Chung, H. S., Raetz, C. R. (2010). "Interchangeable domains in the Kdo transferases of Escherichia coli and Haemophilus influenzae." Biochemistry 49:4126-4137. Pubmed: 20394418
  • Kadrmas, J. L., Raetz, C. R. (1998). "Enzymatic synthesis of lipopolysaccharide in Escherichia coli. Purification and properties of heptosyltransferase i." J Biol Chem 273:2799-2807. Pubmed: 9446588
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID29056
HMDB IDNot Available
Pubchem Compound ID862
Kegg IDC04919
ChemSpider ID8504585
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. 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
Uniprot ID:
P0AC75
Molecular weight:
47291
Protein Details
2. Tetraacyldisaccharide 4'-kinase
General function:
Involved in ATP binding
Specific function:
Transfers the gamma-phosphate of ATP to the 4'-position of a tetraacyldisaccharide 1-phosphate intermediate (termed DS-1- P) to form tetraacyldisaccharide 1,4'-bis-phosphate (lipid IVA)
Gene Name:
lpxK
Uniprot ID:
P27300
Molecular weight:
35589
Reactions
ATP + (2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate) = ADP + (2-N,3-O-bis(3-hydroxytetradecanoyl)-4-O-phosphono-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate).
Protein Details
3. Undecaprenyl phosphate-alpha-4-amino-4-deoxy-L-arabinose arabinosyl transferase
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.