C55-isoprenyl pyrophosphate

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C55-isoprenyl pyrophosphate
Skeletal formula of C55-isoprenyl pyrophosphate
n = 8
Names
Preferred IUPAC name
(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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 trihydrogen diphosphate
Other names
C55-undecaprenyl pyrophosphate; di-trans,poly-cis-undecaprenyl diphosphate; Undecaprenyl pyrophosphate; Pyrophosphoryl undecaprenol; Undecaisoprenyl pyrophosphate; Undecaprenyl diphosphate; Diphosphoundecaprenol; Bactoprenyl diphosphate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • 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-
    Key: NTXGVHCCXVHYCL-NTDVEAECSA-N
  • CC(=CCC/C(=C/CC/C(=C/CC/C(=C\CC/C(=C\CC/C(=C\CC/C(=C\CC/C(=C\CC/C(=C\CC/C(=C\CC/C(=C\COP(=O)(O)OP(=O)(O)O)/C)/C)/C)/C)/C)/C)/C)/C)/C)/C)C
Properties
C55H92O7P2
Molar mass 927.282 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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C55-isoprenyl pyrophosphate (also known as undecaprenyl pyrophosphate or C55-PP) is an essential molecule involved in the construction of the bacterial peptidoglycan cell wall.[1] It is a receptor found in the plasma membrane of bacteria allowing glycan tetrapeptide monomers synthesized in the cell cytoplasm to translocate to the periplasmic space.[2]

C55-P (undecaprenyl phosphate) is a related compound, containing one fewer phosphate group. It is produced from C55-PP by reaction EC 3.6.1.27, typically catalyzed by UppP/BacA. C55-P is recycled back into C55-PP later in the process. C55-OH is known as bactoprenol.[2]

References

  1. ^ Stone, K. John; Strominger, Jack L. (December 1971). "Mechanism of Action of Bacitracin: Complexation with Metal Ion and C55-Isoprenyl Pyrophosphate". PNAS. 68 (12): 3223–3227. Bibcode:1971PNAS...68.3223S. doi:10.1073/pnas.68.12.3223. PMC 389626. PMID 4332017.
  2. ^ a b Manat, Guillaume; Roure, Sophie; Auger, Rodolphe; Bouhss, Ahmed; Barreteau, Hélène; Mengin-Lecreulx, Dominique; Touzé, Thierry (June 2014). "Deciphering the Metabolism of Undecaprenyl-Phosphate: The Bacterial Cell-Wall Unit Carrier at the Membrane Frontier". Microbial Drug Resistance. 20 (3): 199–214. doi:10.1089/mdr.2014.0035. PMC 4050452. PMID 24799078.
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