Reaction #2006447

ord-ab1f590af9384582b9d32b85d5237c0b

Reaction equation

COc1ccc2c(c1)CC(N)CC2
7-methoxy-2-aminotetraline
[Na+].[OH-]
sodium hydroxide
COc1ccc2c(c1)CC(N)CC2
7-methoxy-2-aminotetraline
COc1ccc2c(c1)CC(N)CC2
7-methoxy-2-aminotetraline
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+
O=P([O-])([O-])[O-]
phosphate
C[C@H](N)C(=O)O
L-alanine
Cc1ncc(COP(=O)(O)O)c(C=O)c1O
pyridoxal phosphate
COc1ccc2c(c1)CC(N)CC2
7-methoxy-2-aminotetraline
→
COc1ccc2c(c1)C[C@@H](N)CC2
(S)-7-methoxy-2-aminotetraline

Reactants

COc1ccc2c(c1)CC(N)CC2
7-methoxy-2-aminotetraline
[Na+].[OH-]
sodium hydroxide
COc1ccc2c(c1)CC(N)CC2
7-methoxy-2-aminotetraline
COc1ccc2c(c1)CC(N)CC2
7-methoxy-2-aminotetraline
—
resultant product
—
( S )
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+
O=P([O-])([O-])[O-]
phosphate
C[C@H](N)C(=O)O
L-alanine
Cc1ncc(COP(=O)(O)O)c(C=O)c1O
pyridoxal phosphate
—
bacterial suspension
—
aqueous solution
COc1ccc2c(c1)CC(N)CC2
7-methoxy-2-aminotetraline

Reagents

None

Solvents

O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    workup.ADDITIONwere poured
  2. 2
    workup.ADDITIONwas added so that total volume was 30 ml
  3. 3
    Otherproduced in the reaction liquid
  4. 4
    Otherwas produced

Procedure

Into a flask containing 300 mg of a substrate 7-methoxy-2-tetralone, 460 mg of D-glucose, 3 mg of NAD+, 3 ml of 1 M phosphate buffer solution (with a pH of 7), 910 mg of L-alanine, and 4.0 mg of pyridoxal phosphate, 6 ml of the bacterial suspension were poured, and then deionized water 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. After the reaction, 7-methoxy-2-aminotetraline produced in the reaction liquid was analyzed under the following HPLC conditions, whereby the rate of conversion and optical purity were measured. In the result, it was found that 7-methoxy-2-aminotetraline was produced, but in such a small amount that the rate of conversion into 7-methoxy-2-aminotetraline was 1.5%. The absolute configuration of 7-methoxy-2-aminotetraline was (S), and the optical purity was 74.1% e.e.

Source

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