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Undecaprenyl phosphate

Undecaprenyl phosphate
Names
IUPAC name
[(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-undecaenyl] dihydrogen phosphate
Other names
Undecaprenyl phosphate; 3,7,11,15,19,23,27,31,35,39,43-Undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaun decaen-1-ol, dihydrogen phosphate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C55H91O4P/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,(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: UFPHFKCTOZIAFY-RDQGWRCRSA-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)O)/C)/C)/C)/C)/C)/C)/C)/C)/C)/C)C
Properties
C55H91O4P
Molar mass 847.303 g·mol−1
Related compounds
Related compounds
 C55-isoprenyl pyrophosphate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Undecaprenyl phosphate (UP), also known lipid-P, bactoprenol[1] and C55-P.,[2] is a molecule with the primary function of trafficking polysaccharides across the cell membrane, largely contributing to the overall structure of the cell wall in Gram-positive bacteria. In some situations, UP can also be utilized to carry other cell-wall polysaccharides, but UP is the designated lipid carrier for peptidoglycan. During the process of carrying the peptidoglycan across the cell membrane, N-acetylglucosamine and N-acetylmuramic acid are linked to UP on the cytoplasmic side of the membrane before being carried across.[3] UP works in a cycle of phosphorylation and dephosphorylation as the lipid carrier gets used, recycled, and reacts with undecaprenyl phosphate. This type of synthesis is referred to as de novo synthesis where a complex molecule is created from simpler molecules as opposed to a complete recycle of the entire structure.[3]

The synthesis of UP differs between Gram-negative and Gram-positive bacteria. In Gram-positive bacteria, undecaprenol is found in vast quantities, which is then phosphorylated into UP. For Gram-negative bacteria however, there has yet to be any indication that they contain any undecaprenol at all. Instead of having an undecaprenol be phosphorylated, it appears that instead, Gram-negative bacteria undergo a dephosphorylation of undecaprenyl diphosphate which is catalyzed by both a type-2 phosphatidic acid, phosphatase homologue, and a BacA homologue.[4]

Undecaprenyl phosphate is also known to be the "Universal Glycan Lipid Carrier". When UP is inhibited, the peptidoglycan synthesis is interrupted and it could lead to cell lysis. Furthermore, UP is involved in the metabolism of many cellular processes that can potentially be targeted by antibiotics. Also, it is common for bacteria to use UP to translocate glycan; however, certain bacteria do not use undecaprenyl phosphate as a glycan translocator.[3]

  1. ^ TouzÉ, Thierry; Mengin-Lecreulx, Dominique (2008-02-12). Slauch, James M. (ed.). "Undecaprenyl Phosphate Synthesis". EcoSal Plus. 3 (1): ecosalplus.4.7.1.7. doi:10.1128/ecosalplus.4.7.1.7. ISSN 2324-6200. PMID 26443724.
  2. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).
  3. ^ a b c Manat, Guillaume; Roure, Sophie; Auger, Rodolphe; Bouhss, Ahmed; Barreteau, Hélène; Mengin-Lecreulx, Dominique; Touzé, Thierry (2014-06-01). "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. ISSN 1076-6294. PMC 4050452. PMID 24799078.
  4. ^ Kawakami, Naoki; Fujisaki, Shingo (2018-06-03). "Undecaprenyl phosphate metabolism in Gram-negative and Gram-positive bacteria". Bioscience, Biotechnology, and Biochemistry. 82 (6): 940–946. doi:10.1080/09168451.2017.1401915. ISSN 0916-8451. PMID 29198165. S2CID 13605619.

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