Bactoprenol

Last updated
Bactoprenol
Bactoprenol.svg
Names
IUPAC name
(6Z,10Z,14Z,18Z,22Z,26Z,30Z,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
Other names
Dolichol-11
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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- Yes check.svgY
    Key: BNAIICFZMLQZKW-LSTWDCEHSA-N Yes check.svgY
  • 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-LSTWDCEHSA-N
  • C/C(C)=C/CC/C(C)=C/CC/C(C)=C/CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CC/C(C)=C\CCC(C)CCO
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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]

See also

References

  1. 1 2 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. ↑ Kaiser, Gary (September 2018). "BIOL 230 Lecture Guide - Synthesis of Peptidoglycan - Role of Bactoprenol". faculty.ccbcmd.edu. Archived from the original on 2019-08-31. Retrieved 2018-12-20.
  3. ↑ Jaenicke L, Siegmund HU (November 1989). "Synthesis and characterization of dolichols and polyprenols of designed geometry and chain length". Chemistry and Physics of Lipids. 51 (3–4): 159–70. doi:10.1016/0009-3084(89)90003-0.
  4. ↑ Barker DC, Thorne KJ (November 1970). "Spheroplasts of Lactobacillus casei and the cellular distribution of bactoprenol". Journal of Cell Science. 7 (3): 755–85. doi:10.1242/jcs.7.3.755. PMID   4250091.
  5. ↑ Thorne KJ, Barker DC (April 1972). "The occurrence of bactoprenol in the mesosome and plasma membranes of Lactobacillus casei and Lactobacillus plantarum". Journal of General Microbiology. 70 (1): 87–98. doi: 10.1099/00221287-70-1-87 . PMID   4625239.
  6. ↑ Kaiser G (September 2018). "BIOL 230 Lecture Guide - Synthesis of Peptidoglycan - Role of Bactoprenol". faculty.ccbcmd.edu. Archived from the original on 2019-08-31. Retrieved 2018-12-20.
  7. ↑ Schneider T, Sahl HG (February 2010). "Lipid II and other bactoprenol-bound cell wall precursors as drug targets". Current Opinion in Investigational Drugs. 11 (2): 157–64. PMID   20112165.
  8. ↑ Schneider T, Gries K, Josten M, Wiedemann I, Pelzer S, Labischinski H, Sahl HG (April 2009). "The lipopeptide antibiotic Friulimicin B inhibits cell wall biosynthesis through complex formation with bactoprenol phosphate". Antimicrobial Agents and Chemotherapy. 53 (4): 1610–8. doi:10.1128/AAC.01040-08. PMC   2663061 . PMID   19164139.
  9. ↑ Scherer K, Wiedemann I, Ciobanasu C, Sahl HG, Kubitscheck U (November 2013). "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. doi: 10.1016/j.bbamem.2013.07.014 . PMID   23872123.
  10. ↑ Münch D, Müller A, Schneider T, Kohl B, Wenzel M, Bandow JE, Maffioli S, Sosio M, Donadio S, Wimmer R, Sahl HG (April 2014). "The lantibiotic NAI-107 binds to bactoprenol-bound cell wall precursors and impairs membrane functions". The Journal of Biological Chemistry. 289 (17): 12063–76. doi: 10.1074/jbc.M113.537449 . PMC   4002112 . PMID   24627484.
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