Methanophenazine

Methanophenazine, a phenazine derivative, is a strongly hydrophobic redox-active cofactor with a role in electron transport in some methanogens.[1] This chromophore can be purified from membranes of methanogenic archaea such as Methanosarcina mazei. The enzyme methanosarcina-phenazine hydrogenase (EC 1.12.98.3) has the name methanophenazine hydrogenase as a synonym.

Methanophenazine
Names
IUPAC name
2-{[(3S,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-6,10,14,18-tetraen-1-yl]oxy}phenazine
Other names
(−)-(S)-Methanophenazine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C37H50N2O/c1-28(2)13-9-14-29(3)15-10-16-30(4)17-11-18-31(5)19-12-20-32(6)25-26-40-33-23-24-36-37(27-33)39-35-22-8-7-21-34(35)38-36/h7-8,13,15,17,19,21-24,27,32H,9-12,14,16,18,20,25-26H2,1-6H3/b29-15+,30-17+,31-19+
  • C[C@@H](CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/C)CCOC1=CC2=NC3=CC=CC=C3N=C2C=C1
Properties
C37H50N2O
Molar mass 538.820 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Beifuss, Uwe; Tietze, Mario; Baumer, Sebastian; Deppenmeier, Uwe (2000). "Methanophenazine: structure, total synthesis, and function of a new cofactor from methanogenic Archaea". Angewandte Chemie International Edition. 39 (14): 2470–2472. doi:10.1002/1521-3773(20000717)39:14<2470::AID-ANIE2470>3.0.CO;2-R. PMID 10941105.


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