Di-trans,poly-cis-undecaprenyl phosphate (ECMDB20310) (M2MDB001145)
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Version | 2.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Creation Date | 2012-05-31 14:38:34 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 2015-06-03 17:19:45 -0600 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Secondary Accession Numbers |
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Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Di-trans,poly-cis-undecaprenyl phosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | Di-trans,poly-cis-undecaprenyl phosphate is an undecaprenyl phosphate having two (E)- and eight (Z)-double bonds. It is invovled in Peptidoglycan biosynthesis. (KEGG). Escherichia coli and other Gram-negative bacteria utilize the methylerythritol phosphate pathway to synthesize isopentenyl diphosphate and dimethylallyl diphosphate which are the precursors of (2E,6E)-farnesyl diphosphate. The latter compound is a precursor of di-trans,poly-cis-undecaprenyl phosphate, which leads to the biosynthesis of cell wall polymers. Initially (2E,6E)-farnesyl diphosphate is formed by the joining of geranyl diphosphate and isopentenyl diphosphate in a reaction catalyzed by geranyl diphosphate synthase / farnesyl diphosphate synthase encoded by gene ispA. Subsequently multiple units of isopentenyl diphosphate are polymerized to form di-trans,octa-cis-undecaprenyl diphosphate in a series of sequential condensation reactions catalyzed by undecaprenyl diphosphate synthase encoded by gene ispU. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C55H89O4P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Weight: | Average: 845.2665 Monoisotopic: 844.649847848 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | DCZTULDWWVSYKM-UHFFFAOYSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C55H89O4P/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-59-60(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3/q-1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | {dioxo[(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl)oxy]-λ⁵-phosphanuidyl}oxidanyl | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | {dioxo[(3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl)oxy]-λ⁵-phosphanuidyl}oxidanyl | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCCC(C)=CCO[P-]([O])(=O)=O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description | belongs to the class of organic compounds known as polyterpenoids. These are terpenoids consisting of more than eight isoprene units. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Lipids and lipid-like molecules | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Prenol lipids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Polyterpenoids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Polyterpenoids | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Membrane | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | di-trans,poly-cis-Undecaprenyl diphosphate + Water + Undecaprenyl diphosphate <> Di-trans,poly-cis-undecaprenyl phosphate + Phosphate UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate + UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) <> Uridine 5'-monophosphate + MurAc(oyl-L-Ala-D-gamma-Glu-L-Lys-D-Ala-D-Ala)-diphospho-undecaprenol + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate <> Uridine 5'-monophosphate + Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose + Di-trans,poly-cis-undecaprenyl phosphate <> Undecaprenyl phosphate alpha-L-Ara4FN + Uridine 5'-diphosphate + 4-Amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate Uridine diphosphate-N-acetylglucosamine + Di-trans,poly-cis-undecaprenyl phosphate <> N-Acetyl-D-glucosaminyldiphosphoundecaprenol + Uridine 5'-monophosphate + N-Acetyl-D-glucosaminyldiphospho-di-trans,octa-cis-undecaprenol Undecaprenyl phosphate alpha-L-Ara4N + 2,3,2'3'-Tetrakis(3-hydroxytetradecanoyl)-D-glucosaminyl-1,6-beta-D-glucosamine 1,4'-bisphosphate <> Lipid IIA + Di-trans,poly-cis-undecaprenyl phosphate Undecaprenyl phosphate alpha-L-Ara4N + Di[3-deoxy-D-manno-octulosonyl]-lipid IV(A) <> alpha-Kdo-(2->4)-alpha-Kdo-(2->6)-[4-P-L-Ara4N]-lipid IVA + Di-trans,poly-cis-undecaprenyl phosphate Hydrogen ion + Lipid A-core + Undecaprenyl diphosphate lipid A-core 1-diphosphate + Di-trans,poly-cis-undecaprenyl phosphate Di-trans,poly-cis-undecaprenyl phosphate + Uridine diphosphate-N-acetylglucosamine <> Undecaprenyl-N-acetyl-alpha-D-glucosaminyl-pyrophosphate + Uridine 5'-monophosphate UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine + Di-trans,poly-cis-undecaprenyl phosphate > N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol + Uridine 5'-monophosphate 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 Uridine 5''-diphospho-{beta}-4-deoxy-4-formamido-L-arabinose + Di-trans,poly-cis-undecaprenyl phosphate > 4-deoxy-4-formamido-α-L-arabinopyranosyl <i>ditrans,octacis</i>-undecaprenyl phosphate + Uridine 5'-diphosphate Undecaprenyl diphosphate + Water > Hydrogen ion + Di-trans,poly-cis-undecaprenyl phosphate + Phosphate 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 UDP-Glucose + Di-trans,poly-cis-undecaprenyl phosphate <> Uridine 5'-monophosphate + alpha-D-Glucopyranosyl-diphospho-ditrans,octacis-undecaprenol di-trans,octa-cis-undecaprenyl diphosphate + Water + Undecaprenyl diphosphate <> Di-trans,poly-cis-undecaprenyl phosphate + Phosphate 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: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
KEGG Pathways: | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
EcoCyc Pathways: |
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Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
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References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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Enzymes
- General function:
- Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
- Specific function:
- First step of the lipid cycle reactions in the biosynthesis of the cell wall peptidoglycan
- Gene Name:
- mraY
- Uniprot ID:
- P0A6W3
- Molecular weight:
- 39875
Reactions
UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) + undecaprenyl phosphate = UMP + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol. |
- General function:
- Involved in catalytic activity
- Specific function:
- Hydrolyzes phosphatidylglycerophosphate, phosphatidic acid, and lysophosphatidic acid; the pattern of activities varies according to subcellular location
- Gene Name:
- pgpB
- Uniprot ID:
- P0A924
- Molecular weight:
- 29021
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate. |
- General function:
- Involved in magnesium ion binding
- Specific function:
- Catalyzes the transfer of the GlcNAc-1-phosphate moiety from UDP-GlcNAc onto the carrier lipid undecaprenyl phosphate (C55-P), yielding GlcNAc-pyrophosphoryl-undecaprenyl (GlcNAc-PP- C55). It is the first lipid-linked intermediate involved in enterobacterial common antigen (ECA) synthesis and an acceptor for the addition of subsequent sugars to complete the biosynthesis of O-antigen. The apparent affinity of WecA for the polyisoprenyl phosphate substrates increases with the polyisoprenyl chain length. WecA is unable to utilize dolichyl phosphate (Dol-P)
- Gene Name:
- wecA
- Uniprot ID:
- P0AC78
- Molecular weight:
- 40957
Reactions
UDP-N-acetyl-D-glucosamine + di-trans,octa-cis-undecaprenyl phosphate = UMP + N-acetyl-D-glucosaminyldiphospho-di-trans,octa-cis-undecaprenol. |
- General function:
- Involved in undecaprenyl-diphosphatase activity
- Specific function:
- Catalyzes the dephosphorylation of undecaprenyl diphosphate (UPP). Confers resistance to bacitracin
- Gene Name:
- uppP
- Uniprot ID:
- P60932
- Molecular weight:
- 29758
Reactions
Undecaprenyl diphosphate + H(2)O = undecaprenyl phosphate + phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Overexpression leads to increased undecaprenyl diphosphatase activity and to increased resistance to bacitracin. May have a preferred substrate other than undecaprenyl diphosphate in vivo
- Gene Name:
- ybjG
- Uniprot ID:
- P75806
- Molecular weight:
- 22398
Reactions
Undecaprenyl diphosphate + H(2)O = undecaprenyl phosphate + phosphate. |
- General function:
- Involved in phosphotransferase activity, for other substituted phosphate groups
- Specific function:
- Catalyzes the transfer of 4-deoxy-4-formamido-L- arabinose from UDP to undecaprenyl phosphate. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
- Gene Name:
- arnC
- Uniprot ID:
- P77757
- Molecular weight:
- 36339
Reactions
UDP-4-deoxy-4-formamido-beta-L-arabinose + di-trans,octa-cis-undecaprenyl phosphate = UDP + 4-deoxy-4-formamido-alpha-L-arabinose di-trans,octa-cis-undecaprenyl phosphate. |
- 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 catalytic activity
- Specific function:
- Specific function unknown
- Gene Name:
- yeiU
- Uniprot ID:
- P76445
- Molecular weight:
- 26759