Bactoprenol

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Bactoprenol
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Molar mass 769.318 g·mol−1

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Bactoprenol also known as dolichol-11 and (isomerically vaguely) C55-isoprenyl alcohol (C55-OH) is a lipid first identified in certain species of lactobacilli.[1] It is a hydrophobic alcohol that plays a key role in the growth of cell walls (peptidoglycan) in Gram-positive bacteria.[2]

The double bonds all have the Z configuration except for the three ω-terminal ones, which are biosynthetically derived from (E,E)-farnesyl diphosphate.[3]

Occurrence

Bactoprenol is a lipid synthesized from mevalonic acid and is the most abundant lipid found in certain species of lactobacilli.[1] Bactoprenol is found in both mesosomal and plasma membranes.[4] Mesosomal and plasma bactoprenol are synthesized independently from each other.[5]

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.[6]

Antibiotic significance

Because bactoprenol is so important for cell growth, numerous antibiotic compounds function by disrupting the bactoprenol-mediated transportation pathway.[7] This strategy was first identified by studying the antibiotic mechanism of friulimicin B.[8] Since then, other antibiotics that make use of a similar mechanism have been identified, including nisin[9] and lantibiotics such as NAI-107.[10]

References

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