Bactoprenol

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	12777-41-2^Y
3D model (Jmol)	Interactive image
ChemSpider	4952635^Y
PubChem	6449977
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+^Y Key: BNAIICFZMLQZKW-CYAIWNQHSA-N^Y InChI=1/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-CYAIWNQHBM
SMILES CC(CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)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).
Y verify (what is ^YN ?)
Infobox references

Bactoprenol is a lipid synthesized by three different species of lactobacilli.^[1] It is a hydrophobic C₅₅ isoprenoid.

Bactoprenol phosphate transports NAM and NAG across the cell membrane during the synthesis of peptidoglycan, by flipping the repeating monomer units from the cytoplasm to the periplasm. Bactoprenol remains in the membrane at all times.^[2]

Bacitracin inhibits the recycling of pyrophosphobactoprenol to the inner leaflet.^[3]

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. doi:10.1042/bj0990123. PMC 1264965. PMID 5965329.
↑ "peptidoglycan biosynthesis".
↑ Robyt, John F (1998). Essentials of Carbohydrate Chemistry. Springer. p. 307.

This article is issued from Wikipedia - version of the 3/27/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.