Reacción #2006448

ord-a2ceb9471f53409da87cfdeae32e1271

Ecuación de reacción

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

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otro(pNMTAPAG), obtained in Example 8, which
  2. 2
    workup.ADDITIONwas added so that total volume was 30 ml

Procedimiento

Into 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 (pNMTAPAG), obtained in Example 8, which expresses MTA, PALDH, and GDH was added so that total volume was 30 ml. The resultant product was stirred at 30° C. for 20 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 92.3%. The absolute configuration of 7-methoxy-2-aminotetraline was (S), and the optical purity was 97.0% e.e.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08168412B2uspto-grants-2012_05