Coenzyme B

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Coenzyme B
Coenzyme B (CoB).svg
Names
IUPAC name
2-[(7-mercapto-1-oxoheptyl)amino]-3-phosphonooxybutanoic acid
Identifiers
3D model (JSmol)
ChemSpider
Properties
C
11
H
22
NO
7
PS
Molar mass 343.333641
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Coenzyme B is a coenzyme required for redox reactions in methanogens. The full chemical name of coenzyme B is 7-mercaptoheptanoylthreoninephosphate.[1] The molecule contains a thiol, which is its principal site of reaction.

Coenzyme B reacts with 2-methylthioethanesulfonate (methyl-Coenzyme M, abbreviated CH
3
–S–CoM
), to release methane in methanogenesis:[2]

CH
3
–S–CoM
+ HS–CoB → CH
4
+ CoB–S–S–CoM

This conversion is catalyzed by the enzyme methyl coenzyme M reductase, which contains cofactor F430 as the prosthetic group.

A related conversion that utilizes both HS-CoB and HS-CoM is the reduction of fumarate to succinate, catalyzed by fumarate reductase:[3]

HS–CoM + HS–CoB + O
2
CCH=CHCO
2
O
2
CCH
2
–CH
2
CO
2
+ CoB–S–S–CoM

References[edit]

  1. ^ Noll KM, Rinehart KL, Tanner RS, Wolfe RS (1986). "Structure of component B (7-mercaptoheptanoylthreonine phosphate) of the methylcoenzyme M methylreductase system of Methanobacterium thermoautotrophicum". Proc. Natl. Acad. Sci. U.S.A. 83 (12): 4238–42. doi:10.1073/pnas.83.12.4238. PMC 323707. PMID 3086878.
  2. ^ Thauer RK (September 1998). "Biochemistry of methanogenesis: a tribute to Marjory Stephenson. 1998 Marjory Stephenson Prize Lecture". Microbiology. 144 (Pt 9): 2377–406. doi:10.1099/00221287-144-9-2377. PMID 9782487.
  3. ^ Heim S, Künkel A, Thauer RK, Hedderich R (April 1998). "Thiol:fumarate reductase (Tfr) from Methanobacterium thermoautotrophicum—identification of the catalytic sites for fumarate reduction and thiol oxidation". Eur. J. Biochem. 253 (1): 292–9. doi:10.1046/j.1432-1327.1998.2530292.x. PMID 9578488.