4-Oxobutanoic acid → 4-Oxobutanoic acid

HRID 388192

Reaction equation

[CH2:1]([CH:6]=[O:7])[CH2:2][C:3]([OH:5])=[O:4].CC([C@@H](O)C(NCCC(NCCS)=O)=O)(COP(OP(OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1OP(O)(O)=O)(O)=O)(O)=O)C.C(SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@@H](N2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1OP(O)(O)=O)(=O)CC[C:59]([OH:61])=[O:60]>>[CH2:1]([CH:6]=[O:7])[CH2:2][C:3]([OH:5])=[O:4].[O:7]=[C:6]([CH2:1][CH2:2][C:3]([O-:5])=[O:4])[C:59]([O-:61])=[O:60]

Participants

Reactant 3

HCID 11124-Oxobutanoic acid2×

HCID 87642Coenzyme A

HCID 92133Succinyl CoA

Product 2

HCID 11124-Oxobutanoic acid

HCID 164533Alpha-Ketoglutarate

Procedure

The routes detailed in FIG. 12 are able to achieve the maximum theoretical 6-ACA yield of 0.8 moles 6-ACA per mole glucose utilized. The energetic yield is also favorable, with a maximum of 1.6 moles ATP per mole glucose utilized at the maximum product yield. The following assumptions were used to calculate yield: 1) phosphoenolpyruvate (PEP) carboxykinase is able to operate in the ATP-generating direction, 2) NH4 and 6-ACA are transported into the cell by proton antiport, and 3) succinic semialdehyde is formed from alpha-ketoglutarate and/or succinyl-CoA. Succinic semialdehyde dehydrogenase is a NAD(P)H and CoA-dependent aldehyde dehydrogenase that converts succinyl-CoA to succinic semialdehyde. Succinic semialdehyde is formed from alpha-ketoglutarate by two enzymes: alpha-ketoglutarate decarboxylase and 4-aminobutyrate transaminase.

Sources & evidence

ORD record: ord-00c0336a56b74d99bb0d2ecd4fe91116
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377680B2

Linked notes

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