Bactoprenol: Difference between revisions

| verifiedrevid = 453576743

| ImageFile = Bactoprenol.svg

| ImageSize = 240px

| IUPACName = (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

| OtherNames = Dolichol-11

| CASNo_Ref = {{cascite|correct|cas}}

| CASNo= 12777-41-2

| PubChem=91819839

| 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

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 58837499

| 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-

| InChIKey = BNAIICFZMLQZKW-LSTWDCEHSA-N

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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-

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = BNAIICFZMLQZKW-LSTWDCEHSA-N}}

'''Bactoprenol''' also known as '''dolichol-11''' and (isomerically vaguely) '''C55-isoprenyl alcohol''' (C55-OH) is a [[lipid]] first identified in certain species of [[Lactobacillus|lactobacilli]].<ref name = "Thorne_1966">{{cite journal | vauthors = Thorne KJ, Kodicek E | title = The structure of bactoprenol, a lipid formed by lactobacilli from mevalonic acid | journal = The Biochemical Journal | volume = 99 | issue = 1 | pages = 123–7 | date = April 1966 | doi = 10.1042/bj0990123 | pmid = 5965329 | pmc = 1264965 }}</ref> It is a [[Hydrophobe|hydrophobic]] [[Alcohol (chemistry)|alcohol]] that plays a key role in the growth of [[cell walls]] ([[peptidoglycan]]) in [[Gram-positive bacteria]].<ref>{{Cite web|url=http://faculty.ccbcmd.edu/courses/bio141/lecguide/unit2/control/bactopren_ill_02.html|title=BIOL 230 Lecture Guide - Synthesis of Peptidoglycan - Role of Bactoprenol|last=Kaiser|first=Gary|date=September 2018|website=faculty.ccbcmd.edu|access-date=2018-12-20|archive-date=2019-08-31|archive-url=https://web.archive.org/web/20190831142734/http://faculty.ccbcmd.edu/courses/bio141/lecguide/unit2/control/bactopren_ill_02.html|url-status=dead}}</ref>

The double bonds all have the [[E–Z notation|Z configuration]] except for the three ω-terminal ones, which are [[biosynthesis|biosynthetically]] derived from (E,E)-[[farnesyl diphosphate]].<ref>{{cite journal | vauthors = Jaenicke L, Siegmund HU | title = Synthesis and characterization of dolichols and polyprenols of designed geometry and chain length. | journal = Chemistry and Physics of Lipids | date = November 1989 | volume = 51 | issue = 3–4 | pages = 159–70 | doi = 10.1016/0009-3084(89)90003-0 }}</ref>

== Occurrence ==

Bactoprenol is a lipid synthesized from [[mevalonic acid]] and is the most abundant lipid found in certain species of [[lactobacilli]].<ref name = "Thorne_1966" /> Bactoprenol is found in both [[mesosome|mesosomal]] and [[plasma membranes]].<ref>{{cite journal | vauthors = Barker DC, Thorne KJ | title = Spheroplasts of Lactobacillus casei and the cellular distribution of bactoprenol | journal = Journal of Cell Science | volume = 7 | issue = 3 | pages = 755–85 | date = November 1970 | pmid = 4250091 | doi = 10.1242/jcs.7.3.755}}</ref> Mesosomal and plasma bactoprenol are synthesized independently from each other.<ref>{{cite journal | vauthors = Thorne KJ, Barker DC | title = The occurrence of bactoprenol in the mesosome and plasma membranes of Lactobacillus casei and Lactobacillus plantarum | journal = Journal of General Microbiology | volume = 70 | issue = 1 | pages = 87–98 | date = April 1972 | pmid = 4625239 | doi = 10.1099/00221287-70-1-87 | doi-access = free }}</ref>

== 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.<ref>{{Cite web|url=http://faculty.ccbcmd.edu/courses/bio141/lecguide/unit2/control/bactopren_ill_02.html|title=BIOL 230 Lecture Guide - Synthesis of Peptidoglycan - Role of Bactoprenol|last=Kaiser|first=Gary|name-list-style=vanc|date=September 2018|website=faculty.ccbcmd.edu|access-date=2018-12-20|archive-date=2019-08-31|archive-url=https://web.archive.org/web/20190831142734/http://faculty.ccbcmd.edu/courses/bio141/lecguide/unit2/control/bactopren_ill_02.html|url-status=dead}}</ref>

== Antibiotic significance ==

Because bactoprenol is so important for cell growth, numerous [[antibiotic]] compounds function by disrupting the bactoprenol-mediated transportation pathway.<ref>{{cite journal | vauthors = Schneider T, Sahl HG | title = Lipid II and other bactoprenol-bound cell wall precursors as drug targets | journal = Current Opinion in Investigational Drugs | volume = 11 | issue = 2 | pages = 157–64 | date = February 2010 | pmid = 20112165 }}</ref> This strategy was first identified by studying the antibiotic mechanism of [[Friulimicin|friulimicin B]].<ref>{{cite journal | vauthors = Schneider T, Gries K, Josten M, Wiedemann I, Pelzer S, Labischinski H, Sahl HG | title = The lipopeptide antibiotic Friulimicin B inhibits cell wall biosynthesis through complex formation with bactoprenol phosphate | journal = Antimicrobial Agents and Chemotherapy | volume = 53 | issue = 4 | pages = 1610–8 | date = April 2009 | pmid = 19164139 | doi = 10.1128/AAC.01040-08 | pmc = 2663061 }}</ref> Since then, other antibiotics that make use of a similar mechanism have been identified, including [[nisin]]<ref>{{cite journal | vauthors = Scherer K, Wiedemann I, Ciobanasu C, Sahl HG, Kubitscheck U | title = Aggregates of nisin with various bactoprenol-containing cell wall precursors differ in size and membrane permeation capacity | journal = Biochimica et Biophysica Acta (BBA) - Biomembranes | volume = 1828 | issue = 11 | pages = 2628–36 | date = November 2013 | pmid = 23872123 | doi = 10.1016/j.bbamem.2013.07.014 | doi-access = free }}</ref> and [[lantibiotics]] such as [[NAI-107]].<ref>{{cite journal | vauthors = Münch D, Müller A, Schneider T, Kohl B, Wenzel M, Bandow JE, Maffioli S, Sosio M, Donadio S, Wimmer R, Sahl HG | title = The lantibiotic NAI-107 binds to bactoprenol-bound cell wall precursors and impairs membrane functions | journal = The Journal of Biological Chemistry | volume = 289 | issue = 17 | pages = 12063–76 | date = April 2014 | pmid = 24627484 | doi = 10.1074/jbc.M113.537449 | doi-access = free | pmc = 4002112 }}</ref>

== References ==

{{Reflist}}

[[Category:Fatty alcohols]]

[[Category:Terpenes and terpenoids]]