Coenzyme B

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Coenzyme B
Names
IUPAC name
2-[(7-mercapto-1-oxoheptyl)amino]-3-phosphonooxybutanoic acid
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • 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) checkY
    Key: JBJSVEVEEGOEBZ-UHFFFAOYSA-N checkY
  • 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
  • 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
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 checkY☒N ?)

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

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 experiment 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. PMID 3086878
    .
  2. PMID 9782487
    .
  3. PMID 9578488
    .
  4. PMID 21090696.[permanent dead link
    ]
  5. PMID 20707311
    .
  6. PMID 11669624.[permanent dead link
    ]


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