C55-isoprenyl pyrophosphate

C55-isoprenyl pyrophosphate (undecaprenyl pyrophosphate) is an essential molecule involved in construction of the bacterial peptidoglycan cell wall.[1] It is a receptor found in the plasma membrane of bacteria that allows glycan tetrapeptide monomers synthesized in the cell cytoplasm to translocate to the periplasmic space.

C55-isoprenyl pyrophosphate
Names
Preferred 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-undecaen-1-yl trihydrogen diphosphate
Other names
C55-undecaprenyl pyrophosphate; Undecaprenyl pyrophosphate; Pyrophosphoryl undecaprenol; Undecaisoprenyl pyrophosphate; Undecaprenyl 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+ N
    Key: NTXGVHCCXVHYCL-RDQGWRCRSA-N N
  • InChI=1/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-RDQGWRCRBJ
  • 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).
N verify (what is YN ?)
Infobox references

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.
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