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Literature summary for 1.4.1.9 extracted from

  • Parker, W.; Hanson, R.; Goldberg, S.; Tully, T.; Goswami, A.
    Preparation of (S)-1-cyclopropyl-2-methoxyethanamine by a chemoenzymatic route using leucine dehydrogenase (2012), Org. Process Res. Dev., 16, 464-469.
No PubMed abstract available

Application

Application Comment Organism
synthesis preparation of (S)-1-cyclopropyl-2-methoxyethanamine, a key chiral intermediate for the synthesis of a corticotropin releasing factor-1 (CRF-1) receptor antagonist, by a chemoenzymatic route using leucine dehydrogenase. Synthesis of (S)-1-cyclopropyl-2-methoxyethanamine starting from methylcyclopropyl ketone. Permanganate oxidation of the ketone gives cyclopropylglyoxylic acid, which is converted to (S)-cyclopropylglycine by reductive amination using leucine dehydrogenase from Thermoactinomyces intermedius, recombinantly expressed in Escherichia coli, with NADH cofactor recycling by formate dehydrogenase from Pichia pastoris Thermoactinomyces intermedius

Cloned(Commentary)

Cloned (Comment) Organism
recombinant expression in Escherichia coli strain SC16591 Thermoactinomyces intermedius

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
L-leucine + H2O + NAD+ Thermoactinomyces intermedius
-
4-methyl-2-oxopentanoate + NH3 + NADH + H+
-
?
additional information Thermoactinomyces intermedius synthesis of (S)-1-cyclopropyl-2-methoxyethanamine starting from methylcyclopropyl ketone. Permanganate oxidation of the ketone gives cyclopropylglyoxylic acid, which is converted to (S)-cyclopropylglycine by reductive amination using leucine dehydrogenase from Thermoactinomyces intermedius with NADH cofactor recycling by formate dehydrogenase from Pichia pastoris ?
-
?

Organism

Organism UniProt Comment Textmining
Thermoactinomyces intermedius
-
-
-

Specific Activity [micromol/min/mg]

Specific Activity Minimum [µmol/min/mg] Specific Activity Maximum [µmol/min/mg] Comment Organism
additional information
-
comparing extract activities with 5 mM 2-oxoisovalerate (3282 U/mL) versus 5 mM cyclopropylglyoxylic acid (86 U/mL), leucine dehydrogenase is 38fold more active with the natural substrate Thermoactinomyces intermedius

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
L-leucine + H2O + NAD+
-
Thermoactinomyces intermedius 4-methyl-2-oxopentanoate + NH3 + NADH + H+
-
?
additional information synthesis of (S)-1-cyclopropyl-2-methoxyethanamine starting from methylcyclopropyl ketone. Permanganate oxidation of the ketone gives cyclopropylglyoxylic acid, which is converted to (S)-cyclopropylglycine by reductive amination using leucine dehydrogenase from Thermoactinomyces intermedius with NADH cofactor recycling by formate dehydrogenase from Pichia pastoris Thermoactinomyces intermedius ?
-
?
additional information comparing extract activities with 5 mM 2-oxoisovalerate (3282 U/mL) versus 5 mM cyclopropylglyoxylic acid (86 U/mL), leucine dehydrogenase is 38fold more active with the natural substrate Thermoactinomyces intermedius ?
-
?

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
9
-
with cyclopropylglyoxylic acid as substrate, recombinant enzyme Thermoactinomyces intermedius

pH Range

pH Minimum pH Maximum Comment Organism
7.5 10 activity range, profile, overview Thermoactinomyces intermedius

Cofactor

Cofactor Comment Organism Structure
NAD+
-
Thermoactinomyces intermedius
NADH
-
Thermoactinomyces intermedius