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
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 [77 °F], 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]

  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.