Bactoprenol also known as dolichol-11 and (isomerically vaguely) C55-isoprenyl alcohol (C55-OH) is a
lipid
Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids includ ...
first identified in certain species of
lactobacili.
It is a
hydrophobic
In chemistry, hydrophobicity is the physical property of a molecule that is seemingly repelled from a mass of water (known as a hydrophobe). In contrast, hydrophiles are attracted to water.
Hydrophobic molecules tend to be nonpolar and, t ...
alcohol that plays a key role in the growth of
cell walls (
peptidoglycan
Peptidoglycan or murein is a unique large macromolecule, a polysaccharide, consisting of sugars and amino acids that forms a mesh-like peptidoglycan layer outside the plasma membrane, the rigid cell wall (murein sacculus) characteristic of most ba ...
) in
Gram-positive bacteria.
The double bonds all have the
Z configuration except for the three ω-terminal ones, which are
biosynthetically derived from (E,E)-
farnesyl diphosphate.
Occurrence
Bactoprenol is a lipid synthesized from
mevalonic acid and is the most abundant lipid found in certain species of
lactobacilli.
Bactoprenol is found in both
mesosomal and
plasma membranes. Mesosomal and plasma bactoprenol are synthesized independently from each other.
Function
Bactoprenol is thought to play a key role in the formation of cell walls in gram-positive bacteria by cycling peptidoglycan monomers through the plasma membrane and inserting these monomers at points of growth in the bacterial cell wall.
Antibiotic significance
Because bactoprenol is so important for cell growth, numerous
antibiotic compounds function by disrupting the bactoprenol-mediated transportation pathway. This strategy was first identified by studying the antibiotic mechanism of
friulimicin B. Since then, other antibiotics that make use of a similar mechanism have been identified, including
nisin
Nisin is a polycyclic antibacterial peptide produced by the bacterium ''Lactococcus lactis'' that is used as a food preservative. It has 34 amino acid residues, including the uncommon amino acids lanthionine (Lan), methyllanthionine (MeLan), di ...
and
lantibiotics
Lantibiotics are a class of polycyclic peptide antibiotics that contain the characteristic thioether amino acids lanthionine or methyllanthionine, as well as the Saturated and unsaturated compounds, unsaturated amino acids dehydroalanine, and 2-Am ...
such as
NAI-107.
References
{{Reflist
Fatty alcohols
Terpenes and terpenoids