Bactoprenol

In today's world, Bactoprenol has become a topic of great relevance and interest to a wide range of people. From its impact on society to its influence on popular culture, Bactoprenol has captured the attention of many and generated passionate debates in different areas. In this article, we will comprehensively explore the various facets of Bactoprenol, analyzing its evolution over time, its relevance today, and its possible implications for the future. Additionally, we will examine different perspectives and opinions on Bactoprenol to offer our readers a complete and balanced view on this fascinating topic.

Bactoprenol
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
  • 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- checkY
    Key: BNAIICFZMLQZKW-LSTWDCEHSA-N checkY
  • 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 , 100 kPa).
checkY verify (what is checkY☒N ?)

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

  1. ^ a b 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.