Coenzyme B

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

Names
IUPAC name 2-[(7-mercapto-1-oxoheptyl)amino]-3-phosphonooxybutanoic acid
Identifiers
CAS Number	104302-77-4 Y
3D model (JSmol)	Interactive image Interactive image
ChemSpider	343 Y
PubChem CID	350
UNII	9GS022ISQL Y
CompTox Dashboard (EPA)	DTXSID70897000
InChI InChI=1S/C11H22NO7PS/c1-8(19-20(16,17)18)10(11(14)15)12-9(13)6-4-2-3-5-7-21/h8,10,21H,2-7H2,1H3,(H,12,13)(H,14,15)(H2,16,17,18) Y Key: JBJSVEVEEGOEBZ-UHFFFAOYSA-N Y InChI=1/C11H22NO7PS/c1-8(19-20(16,17)18)10(11(14)15)12-9(13)6-4-2-3-5-7-21/h8,10,21H,2-7H2,1H3,(H,12,13)(H,14,15)(H2,16,17,18)/t8-,10-/m1/s1 Key: JBJSVEVEEGOEBZ-PSASIEDQBT InChI=1/C11H22NO7PS/c1-8(19-20(16,17)18)10(11(14)15)12-9(13)6-4-2-3-5-7-21/h8,10,21H,2-7H2,1H3,(H,12,13)(H,14,15)(H2,16,17,18) Key: JBJSVEVEEGOEBZ-UHFFFAOYAG
SMILES O=C(N[C@@H](C(=O)O)[C@H](OP(=O)(O)O)C)CCCCCCS O=C(NC(C(=O)O)C(OP(=O)(O)O)C)CCCCCCS
Properties
Chemical formula	C 11H 22NO 7PS
Molar mass	343.333641
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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

Importance of coenzyme B in methanogenesis

Coenzyme B is an important component in the terminal step of methane biogenesis.^[4] It acts as a two electron-donor to reduce coenzyme M (methyl-coenzyme) into two molecules a methane and a heterodisulfide.^[5] Two separate experiments that were performed, one with coenzyme B and other without coenzyme B, indicated that using coenzyme B before the formation of the methane molecule, results in a more efficient and consistent bond cleavage.^[6]

References

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". Proceedings of the National Academy of Sciences. 83 (12): 4238–42. Bibcode:1986PNAS...83.4238N. 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". European Journal of Biochemistry. 253 (1): 292–9. doi:10.1046/j.1432-1327.1998.2530292.x. PMID 9578488.
4. Dey, Mishtu; Li, Xianghui; Kunz, Ryan C; Ragsdale, Stephen W (2010-12-22). "Detection of Organometallic and Radical Intermediates in the Catalytic Mechanism of Methyl-Coenzyme M Reductase Using the Natural Substrate Methyl-Coenzyme M and a Coenzyme B Substrate Analogue". Biochemistry. 49 (51): 10902–10911. doi:10.1021/bi101562m. PMID 21090696.^{[permanent dead link‍]}
5. Cedervall, Peder E; Dey, Mishtu; Pearson, Arwen R; Ragsdale, Stephen W; Wilmot, Carrie M (2010-07-22). "Structural Insight into Methyl-Coenzyme M Reductase Chemistry Using Coenzyme B Analogues". Biochemistry. 49 (35): 7683–7693. doi:10.1021/bi100458d. PMC 3098740. PMID 20707311.
6. Horng, Yih-Chern; Becker, Donald F; Ragsdale, Stephen W (2001-10-30). "Mechanistic Studies of Methane Biogenesis by Methyl-Coenzyme M Reductase: Evidence that Coenzyme B Participates in Cleaving the C−S Bond of Methyl-Coenzyme M". Biochemistry. 40 (43): 12875–12885. doi:10.1021/bi011196y. PMID 11669624.^{[permanent dead link‍]}