Reaction #2006458

ord-9290007c1ef24d2dbccd522bdcf1846c

Reaction equation

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[O-].[Na+]
sodium formate
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 )
—
resultant product
—
aqueous solution
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[O-].[Na+]
sodium formate
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

Solvents

O=CO
formic acid

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Other(pNMTAPAF), obtained in Example 29, which
  2. 2
    workup.ADDITIONwas added so that total volume was 30 ml

Procedure

Into a flask containing 520 mg of a substrate 7-methoxy-2-tetralone, 10 mg of sodium formate, 3 mg of NAD+, 1.57 mg of L-alanine, and 20 mg of pyridoxal phosphate, a culture fluid of the recombinant E. coli HB101 (pNMTAPAF), obtained in Example 29, which expresses MTA, PALDH, and FDH was added so that total volume was 30 ml. The resultant product was stirred at 35° C. for 28 hours while being adjusted to a pH of 6.3 by drippage of 5 N aqueous solution of formic acid. The rate of conversion into 7-methoxy-2-aminotetraline after the reaction was 92.6%. The absolute configuration of 7-methoxy-2-aminotetraline was (S), and the optical purity was 98.1% e.e.

Source

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