Undecaprenyl diphosphate (PAMDB000394)
Record Information | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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Version | 1.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 1/22/2018 11:54:54 AM | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Metabolite ID | PAMDB000394 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Name: | Undecaprenyl diphosphate | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Description: | Undecaprenyl diphosphate belongs to the class of Polyprenyl Phosphates. These are prenol lipids in which the phosphate group is linked to one end of the polyprenol moiety. (inferred from compound structure)C55-isoprenyl pyrophosphate (undecaprenyl pyrophosphate) is an essential molecule involved in construction of the bacterial peptidoglycan cell wall. (WikiPedia) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C55H92O7P2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Average Molecular Weight: | 927.2623 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Monoisotopic Molecular Weight: | 926.631828322 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | NTXGVHCCXVHYCL-RDQGWRCRSA-N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C55H92O7P2/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)43-44-61-64(59,60)62-63(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,(H,59,60)(H2,56,57,58)/b46-25+,47-27+,48-29+,49-31+,50-33+,51-35+,52-37+,53-39+,54-41+,55-43+ | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
CAS number: | 23-13-2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | {[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,34E,38E)-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})phosphoryl]oxy}phosphonic acid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | undecaprenyl pyrophosphate | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
SMILES: | CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\CC\C(C)=C\COP(O)(=O)OP(O)(O)=O | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Taxonomy Description | This compound belongs to the class of organic compounds known as bactoprenol diphosphates. These are polyprenyl compounds consisting of a diphosphate group substituted by a bactoprenyl moiety. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Super Class | Lipids and lipid-like molecules | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Prenol lipids | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Polyprenols | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Bactoprenol diphosphates | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Membrane | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + two linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) > Hydrogen ion + Undecaprenyl diphosphate + three linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) 2 Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine >2 Hydrogen ion +2 Undecaprenyl diphosphate + two linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) Water + Undecaprenyl diphosphate > Hydrogen ion + Phosphate + Undecaprenyl phosphate (O16 antigen)x2 undecaprenyl diphosphate + O16 antigen undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x3 undecaprenyl diphosphate + Undecaprenyl diphosphate (O16 antigen)x3 undecaprenyl diphosphate + O16 antigen undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x4 undecaprenyl diphosphate + Undecaprenyl diphosphate 2 O16 antigen undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x2 undecaprenyl diphosphate + Undecaprenyl diphosphate (enterobacterial common antigen)x2 undecaprenyl-diphosphate + Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose > (enterobacterial common antigen)x3 undecaprenyl-diphosphate + Hydrogen ion + Undecaprenyl diphosphate (enterobacterial common antigen)x3 undecaprenyl-diphosphate + Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose > (enterobacterial common antigen)x4 undecaprenyl-diphosphate + Hydrogen ion + Undecaprenyl diphosphate 2 Undecaprenyl-diphospho N-acetylglucosamine-N-acetylmannosaminuronate-N-acetamido-4,6-dideoxy-D-galactose > (enterobacterial common antigen)x2 undecaprenyl-diphosphate + Hydrogen ion + Undecaprenyl diphosphate Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate >8 Pyrophosphate + Undecaprenyl diphosphate core oligosaccharide lipid A + Undecaprenyl diphosphate > core oligosaccharide lipid A diphosphate + Undecaprenyl phosphate core oligosaccharide lipid A + (enterobacterial common antigen)x4 undecaprenyl-diphosphate > (enterobacterial common antigen)x4 core oligosaccharide lipid A + Hydrogen ion + Undecaprenyl diphosphate core oligosaccharide lipid A + (O16 antigen)x4 undecaprenyl diphosphate > Hydrogen ion + (O16 antigen)x4 core oligosaccharide lipid A + Undecaprenyl diphosphate di-trans,poly-cis-Undecaprenyl diphosphate + Water + Undecaprenyl diphosphate <> Di-trans,poly-cis-undecaprenyl phosphate + Phosphate Farnesyl pyrophosphate + 8 Isopentenyl pyrophosphate <> di-trans,poly-cis-Undecaprenyl diphosphate +8 Pyrophosphate + Undecaprenyl diphosphate a peptidoglycan + <i>N</i>-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine-diphosphoundecaprenyl-<i>N</i>-acetylglucosamine > Undecaprenyl diphosphate + a peptidoglycan a peptidoglycan dimer (<I>meso</I>-diaminopimelate containing) + Water > a peptidoglycan with D,D cross-links (<I>meso</I>-diaminopimelate containing) + Undecaprenyl diphosphate + D-Alanine N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine-diphosphoundecaprenyl-N-acetylglucosamine > Hydrogen ion + a peptidoglycan dimer (<I>meso</I>-diaminopimelate containing) + Undecaprenyl diphosphate Undecaprenyl diphosphate + Water > Hydrogen ion + Di-trans,poly-cis-undecaprenyl phosphate + Phosphate (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n)-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol > (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n+1)-diphosphoundecaprenol + Undecaprenyl diphosphate [GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-g-D-Glu-L-Lys-D-Ala-D-Ala)]n-diphosphoundecaprenol + Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine <> Undecaprenyl diphosphate More...2 lipid II(A) > Undecaprenyl diphosphate + Hydrogen ion + a peptidoglycan dimer (meso-diaminopimelate containing) | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Pathways: | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 catalytic activity
- Specific function:
- Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)
- Gene Name:
- mrcB
- Locus Tag:
- PA4700
- Molecular weight:
- 85.5 kDa
Reactions
(GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n)-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n+1)-diphosphoundecaprenol + undecaprenyl diphosphate. |
- General function:
- Involved in penicillin binding
- Specific function:
- Cell wall formation. Essential for the formation of a septum of the murein sacculus. Synthesis of cross-linked peptidoglycan from the lipid intermediates
- Gene Name:
- ftsI
- Locus Tag:
- PA4418
- Molecular weight:
- 62.9 kDa
Reactions
(GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n)-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n+1)-diphosphoundecaprenol + undecaprenyl diphosphate. |
- General function:
- Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
- Specific function:
- Generates undecaprenyl pyrophosphate (UPP) from isopentenyl pyrophosphate (IPP). UPP is the precursor of glycosyl carrier lipid in the biosynthesis of bacterial cell wall polysaccharide components such as peptidoglycan and lipopolysaccharide
- Gene Name:
- uppS
- Locus Tag:
- PA3652
- Molecular weight:
- 28 kDa
Reactions
(2E,6E)-farnesyl diphosphate + 8 isopentenyl diphosphate = 8 diphosphate + di-trans,octa-cis-undecaprenyl diphosphate. |
- General function:
- Involved in undecaprenyl-diphosphatase activity
- Specific function:
- Catalyzes the dephosphorylation of undecaprenyl diphosphate (UPP). Confers resistance to bacitracin
- Gene Name:
- uppP
- Locus Tag:
- PA1959
- Molecular weight:
- 30.7 kDa
Reactions
Undecaprenyl diphosphate + H(2)O = undecaprenyl phosphate + phosphate. |
- General function:
- Involved in catalytic activity
- Specific function:
- Cell wall formation. The enzyme has a penicillin- insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a transpeptidase C-terminal domain which may not be functional
- Gene Name:
- pbpC
- Locus Tag:
- PA2272
- Molecular weight:
- 61.1 kDa
- General function:
- Involved in lipid transporter activity
- Specific function:
- Specific function unknown
- Gene Name:
- mviN
- Locus Tag:
- PA4562
- Molecular weight:
- 56.1 kDa
Transporters
- General function:
- Involved in lipid transporter activity
- Specific function:
- Specific function unknown
- Gene Name:
- mviN
- Locus Tag:
- PA4562
- Molecular weight:
- 56.1 kDa