Bactoprenol Explained

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. 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]

Notes and References

  1. Thorne KJ, Kodicek E . The structure of bactoprenol, a lipid formed by lactobacilli from mevalonic acid . The Biochemical Journal . 99 . 1 . 123–7 . April 1966 . 10.1042/bj0990123 . 5965329 . 1264965 .
  2. Web site: BIOL 230 Lecture Guide - Synthesis of Peptidoglycan - Role of Bactoprenol. Kaiser. Gary. September 2018. faculty.ccbcmd.edu. 2018-12-20. 2019-08-31. https://web.archive.org/web/20190831142734/http://faculty.ccbcmd.edu/courses/bio141/lecguide/unit2/control/bactopren_ill_02.html. dead.
  3. Jaenicke L, Siegmund HU . Synthesis and characterization of dolichols and polyprenols of designed geometry and chain length. . Chemistry and Physics of Lipids . November 1989 . 51 . 3–4 . 159–70 . 10.1016/0009-3084(89)90003-0 .
  4. Barker DC, Thorne KJ . Spheroplasts of Lactobacillus casei and the cellular distribution of bactoprenol . Journal of Cell Science . 7 . 3 . 755–85 . November 1970 . 4250091 . 10.1242/jcs.7.3.755.
  5. Thorne KJ, Barker DC . The occurrence of bactoprenol in the mesosome and plasma membranes of Lactobacillus casei and Lactobacillus plantarum . Journal of General Microbiology . 70 . 1 . 87–98 . April 1972 . 4625239 . 10.1099/00221287-70-1-87 . free .
  6. Web site: BIOL 230 Lecture Guide - Synthesis of Peptidoglycan - Role of Bactoprenol. Kaiser. Gary. vanc. September 2018. faculty.ccbcmd.edu. 2018-12-20. 2019-08-31. https://web.archive.org/web/20190831142734/http://faculty.ccbcmd.edu/courses/bio141/lecguide/unit2/control/bactopren_ill_02.html. dead.
  7. Schneider T, Sahl HG . Lipid II and other bactoprenol-bound cell wall precursors as drug targets . Current Opinion in Investigational Drugs . 11 . 2 . 157–64 . February 2010 . 20112165 .
  8. Schneider T, Gries K, Josten M, Wiedemann I, Pelzer S, Labischinski H, Sahl HG . The lipopeptide antibiotic Friulimicin B inhibits cell wall biosynthesis through complex formation with bactoprenol phosphate . Antimicrobial Agents and Chemotherapy . 53 . 4 . 1610–8 . April 2009 . 19164139 . 10.1128/AAC.01040-08 . 2663061 .
  9. Scherer K, Wiedemann I, Ciobanasu C, Sahl HG, Kubitscheck U . Aggregates of nisin with various bactoprenol-containing cell wall precursors differ in size and membrane permeation capacity . Biochimica et Biophysica Acta (BBA) - Biomembranes . 1828 . 11 . 2628–36 . November 2013 . 23872123 . 10.1016/j.bbamem.2013.07.014 . free .
  10. Münch D, Müller A, Schneider T, Kohl B, Wenzel M, Bandow JE, Maffioli S, Sosio M, Donadio S, Wimmer R, Sahl HG . The lantibiotic NAI-107 binds to bactoprenol-bound cell wall precursors and impairs membrane functions . The Journal of Biological Chemistry . 289 . 17 . 12063–76 . April 2014 . 24627484 . 10.1074/jbc.M113.537449 . free . 4002112 .

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