Industrial Biotransformations

Glutamate dehydrogenase / Glucose 1-dehydrogenase
Beef liver / Bacillus megaterium
1) Reaction conditions
[1]: 0.59 M, 100 g · L –1 [168.12 g · mol –1 ] 2-keto-6-hydroxy hexanoic acid, sodium
salt in equilibrium with 2-hydroxytetrahydropyran-2-carboxylic acid, sodium
salt
[2]: 1 M ammonium formate
[3]: reduced nicotinamide adenine dinucleotide NADH
pH: 8.7
medium: aqueous
reaction type: redox reaction
catalyst: enzymes
enzyme: l-glutamic acid dehydrogenase
enzyme: d-glucose dehydrogenase
strain: Beef liver / Bacillus megaterium
CAS (enzyme): [9029-12-3] / [9028-53-9]
2) Remarks
HO
1 = 2-keto-6-hydroxyhexanoic acid, sodium salt
2 = L-6-hydroxynorleucine
Fig. 1.4.1.3 / 1.1.1.118 – 1
● Reductive amination of ketoacid using amino acid dehydrogenases has been shown to be a
useful method for the synthesis of natural and unnatural amino acids.
● 2-Keto-6-hydroxy hexanoic acid was converted completely into l-6-hydroxynorleucine by
phenylalanine dehydrogenase from Sporosarcina sp. or by beef liver glutamate dehydrogenase.
● Beef liver glutamate dehydrogenase was used for preparative reaction at 100 g · L –1 substrate
concentrations.
3) Flow scheme
Not published.
O
O
O - Na +
E1
1 2
gluconic acid
NH 3
NADH NAD +
E2
HO
glucose
NH 2
O
EC 1.4.1.3 / 1.1.1.118
OH
Bristol-Myers Squibb
201