Reaction #2006449

ord-335422b31c2c480089af6e84206884fc

Reaction equation

COc1ccc2c(c1)CC(N)CC2
7-methoxy-2-aminotetraline
COc1ccc2c(c1)CC(N)CC2
7-methoxy-2-aminotetraline
[Na+].[OH-]
sodium hydroxide
COc1ccc2c(c1)CC(=O)CC2
7-methoxy-2-tetralone
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
NC(=O)c1ccc[n+]([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)c1
NAD+
C[C@H](N)C(=O)O
L-alanine
Cc1ncc(COP(=O)(O)O)c(C=O)c1O
pyridoxal phosphate
→
COc1ccc2c(c1)C[C@@H](N)CC2
(S)-7-methoxy-2-aminotetraline

Reactants

—
( S )
COc1ccc2c(c1)CC(N)CC2
7-methoxy-2-aminotetraline
—
resultant product
—
aqueous solution
COc1ccc2c(c1)CC(N)CC2
7-methoxy-2-aminotetraline
[Na+].[OH-]
sodium hydroxide
COc1ccc2c(c1)CC(=O)CC2
7-methoxy-2-tetralone
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
D-glucose
NC(=O)c1ccc[n+]([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)c1
NAD+
C[C@H](N)C(=O)O
L-alanine
Cc1ncc(COP(=O)(O)O)c(C=O)c1O
pyridoxal phosphate

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Other(pNMTA, pSTVPAG), obtained in Example 9, which
  2. 2
    workup.ADDITIONwas added so that total volume was 30 ml

Procedure

To a flask containing 300 mg of a substrate 7-methoxy-2-tetralone, 460 mg of D-glucose, 3 mg of NAD+, 910 mg of L-alanine, and 4.0 mg of pyridoxal phosphate, a culture fluid of the recombinant E. coli HB101 (pNMTA, pSTVPAG), obtained in Example 9, which expresses MTA, PALDH, and GDH was added so that total volume was 30 ml. The resultant product was stirred at 30° C. for 25 hours while being adjusted to a pH of 6.8 by drippage of 5 N aqueous solution of sodium hydroxide. The rate of conversion into 7-methoxy-2-aminotetraline after the reaction was 60.2%. The absolute configuration of 7-methoxy-2-aminotetraline was (S), and the optical purity was 97.1% e.e.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08168412B2uspto-grants-2012_05