Reaktion #1269832

ord-eb07a05c8be14fdcab27a14f2a791c90

Reaktionsgleichung

CC(C)(COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)CCCC(=O)O
3-Hydroxypimeloyl-CoA
CC(C)(COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCC(=O)O
pimeloyl-CoA
CC(C)(COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)CCCC(=O)O
3-hydroxypimelyl-CoA
CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O
acetoacetyl-CoA
→
CC(C)(COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O)C(O)C(=O)NCCC(=O)NCCSC(=O)C1=CCCCC1=O
6-oxocylohex-1-ene-1-carboxyl-CoA

Edukte

CC(C)(COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)CCCC(=O)O
3-Hydroxypimeloyl-CoA
CC(C)(COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCC(=O)O
pimeloyl-CoA
CC(C)(COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)CCCC(=O)O
3-hydroxypimelyl-CoA
CC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](n2cnc3c(N)ncnc32)[C@H](O)[C@@H]1OP(=O)(O)O
acetoacetyl-CoA

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Alternative routes for producing a cyclic compound from 3-hydroxypimeloyl-CoA that do not proceed through pimeloyl-CoA are shown in FIG. 3. This route is found in Geobacter metallireducens and Thauera aromatica, among others, in the direction of beta-oxidation. In the route, the biosynthesis of 3-hydroxypimelyl-CoA proceeds from acetoacetyl-CoA, as described above. 3-Hydroxypimeloyl-CoA is dehydrated to form a cyclic product, 6-oxocylohex-1-ene-1-carboxyl-CoA (6-KCH-CoA). 6-KCH-CoA is then converted to cyclohexanone in three enzymatic steps: removal of the CoA moiety, decarboxylation and reduction. With a reversible PEP carboxykinase, this pathway is predicted to achieve a theoretical yield of cyclohexanone (0.75 mol/mol) and is able to achieve an ATP yield of 0.56 mol/mol if a transferase or ATP synthase is utilized in step 2.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08663957B2uspto-grants-2014_03