Bactoprenol

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Bactoprenol
Bactoprenol2.svg
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
12777-41-2 YesY
ChemSpider 4952635 YesY
Jmol 3D model Interactive image
PubChem 6449977
Properties
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[edit]

  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 1264965free to read. PMID 5965329. 
  2. ^ "peptidoglycan biosynthesis". 
  3. ^ Robyt, John F (1998). Essentials of Carbohydrate Chemistry. Springer. p. 307.