Bactoprenol
 | |
| Names | |
|---|---|
IUPAC name (6E,10E,14E,18E,22E,26E,30E,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 | |
| Identifiers | |
CAS Number |
|
3D model (JSmol) |
|
ChemSpider |
|
PubChem CID |
|
InChI
| |
SMILES
| |
| Properties | |
Chemical formula | 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). | |
 Y verify (what is  Y N ?) | |
Infobox references | |
Bactoprenol is a lipid first identified in certain species of lactobacili.[1] It is a hydrophobic alcohol that plays a key role in the growth of cell membranes in Gram-positive bacteria.[2]
Contents
1 Occurrence
2 Function
3 Antibiotic significance
4 References
Occurrence
Bactoprenol is a lipid synthesized from mevalonic acid and is the most abundant lipid found in certain species of lactobacilli.[3] 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
^ 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. PMC 1264965. PMID 5965329..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output .citation q{quotes:"""""""'""'"}.mw-parser-output .citation .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .citation .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-ws-icon a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-maint{display:none;color:#33aa33;margin-left:0.3em}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}
^ Kaiser, Gary (September 2018). "BIOL 230 Lecture Guide - Synthesis of Peptidoglycan - Role of Bactoprenol". faculty.ccbcmd.edu. Retrieved 2018-12-20.
^ 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. PMC 1264965. PMID 5965329.
^ Barker DC, Thorne KJ (November 1970). "Spheroplasts of Lactobacillus casei and the cellular distribution of bactoprenol". Journal of Cell Science. 7 (3): 755–85. 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. 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. 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. PMID 24627484.
