Bactoprenol

Bactoprenol

Names
IUPAC name (6E,10E,14E,18E,22E,26E,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-6,10,14,18,22,26,30,34,38,42-decaen-1-ol
Identifiers
CAS Number	12777-41-2
ChemSpider	4952635
Jmol interactive 3D	Image
PubChem	6449977
InChI InChI=1S/C55H92O/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)43-44-56/h23,25,27,29,31,33,35,37,39,41,55-56H,13-22,24,26,28,30,32,34,36,38,40,42-44H2,1-12H3/b46-25+,47-27+,48-29+,49-31+,50-33+,51-35+,52-37+,53-39+,54-41+ Key: BNAIICFZMLQZKW-CYAIWNQHSA-N InChI=1/C55H92O/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)43-44-56/h23,25,27,29,31,33,35,37,39,41,55-56H,13-22,24,26,28,30,32,34,36,38,40,42-44H2,1-12H3/b46-25+,47-27+,48-29+,49-31+,50-33+,51-35+,52-37+,53-39+,54-41+ Key: BNAIICFZMLQZKW-CYAIWNQHBM
SMILES CC(CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)CCO
Properties
Chemical formula	C55H92O
Molar mass	769.318 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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Infobox references

Bactoprenol is a lipid synthesized by three different species of lactobacilli.^[1] It is a hydrophobic C₅₅ isoprenoid.

Bactoprenol phosphate transports NAM and NAG across the cell membrane during the synthesis of peptidoglycan, by flipping the repeating monomer units from the cytoplasm to the periplasm. Bactoprenol remains in the membrane at all times.^[2]

Bacitracin inhibits the recycling of pyrophosphobactoprenol to the inner leaflet.^[3]

References

1. Thorne KJ, Kodicek E (April 1966). "The structure of bactoprenol, a lipid formed by lactobacilli from mevalonic acid". The Biochemical Journal 99 (1): 123–7. doi:10.1042/bj0990123. PMC 1264965. PMID 5965329.
2. "peptidoglycan biosynthesis".
3. Robyt, John F (1998). Essentials of Carbohydrate Chemistry. Springer. p. 307.