Propionic Acid → 3-Hydroxybutanoic acid, (R)-

Reaktionsgleichung

O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C(O)(=O)CC.[OH:18][C@H:19]([CH2:24][CH3:25])[CH2:20][C:21]([O-:23])=[O:22]>>[OH:18][C@H:19]([CH3:24])[CH2:20][C:21]([OH:23])=[O:22].[OH:18][C@H:19]([CH2:24][CH3:25])[CH2:20][C:21]([OH:23])=[O:22]

Komponenten

Edukt 3

HCID 1032Propionic Acid

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

HCID 86758581(3R)-3-Hydroxyvalerate

Produkt 2

HCID 921353-Hydroxybutanoic acid, (R)-

HCID 10290775(R)-3-hydroxypentanoic acid

Versuchsvorschrift

Ralstonia eutropha NCIMB 11599 was cultured in a medium containing 10 g/L of glucose and 1 g/L of propionic acid, according to the method previously reported (Kim et al., Enzyme Microbial. Technol., 16: 556-561, 1994). Poly-(R)-(−)-3-hydroxybutyrate-co-(R)-(−)-3-hydroxyvalerate (PHB/V) copolymer (containing 8 mol % (R)-(−)-3-hydroxyvalerate) was accumulated to a content of 63% of cell dry weight, which was auto-degraded to produce (R)-(−)-3-hydroxybutyric acid and (R)-(−)-3-hydroxyvaleric acid. Cells were dispersed in water at a copolymer concentration of 27.4 g/L. Auto-degradation reaction was carried out at pH 7 and 30° C. for 35 hours. As a result, 5.8 g/L of (R)-(−)-3-hydroxybutyric acid and 0.6 g/L of (R)-(−)-3-hydroxyvaleric acid were obtained. Therefore, a mixture of (R)-(−)-3-hydroxybutyric acid and (R)-(−)-3-hydroxyvaleric acid can be efficiently prepared from the accumulated PHB/V polymer by auto-degradation of the copolymer, and they can be separated using LC or HPLC (Ref. Example 16).