Bactoprenol
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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
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Other names
Dolichol-11
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
PubChem CID
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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).
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Bactoprenol also known as dolichol-11 and (isomerically vaguely) C55-isoprenyl alcohol (C55-OH) is a
The double bonds all have the
Occurrence
Bactoprenol is a lipid synthesized from
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
- ^ 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.
- .
- PMID 4250091.
- 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.
- PMID 20112165.
- PMID 19164139.
- PMID 23872123.
- PMID 24627484.