Bactoprenol

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
CAS Number	12777-41-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	58837499 ;
PubChem CID	91819839;
	InChI 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 ; 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;
	SMILES 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
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). verify (what is ?) Infobox references

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

^ ^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.
^ 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.
^ 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. Archived from the original on 2019-08-31. 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.

[Thorne_1966-1] 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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