Bactoprenol
Chemical compound
Names | |
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IUPAC name
(6
Z
,10
Z
,14
Z
,18
Z
,22
Z
,26
Z
,30
Z
,34
E
,38
E
)-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
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Other names
Dolichol-11
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Identifiers | |
3D model (
JSmol
)
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ChemSpider |
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PubChem
CID
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Properties | |
C 55 H 92 O | |
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).
|
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 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 .
- ↑ Kaiser, Gary (September 2018). "BIOL 230 Lecture Guide - Synthesis of Peptidoglycan - Role of Bactoprenol" . faculty.ccbcmd.edu . Retrieved 2018-12-20 .
- ↑ 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 .
- ↑ 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 .
- ↑ 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 .
- ↑ Kaiser G (September 2018). "BIOL 230 Lecture Guide - Synthesis of Peptidoglycan - Role of Bactoprenol" . faculty.ccbcmd.edu . Retrieved 2018-12-20 .
- ↑ 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 .
- ↑ 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 .
- ↑ 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 .
- ↑ 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 .