Pyridoxal 5'-phosphate → (S)-7-methoxy-2-aminotetraline

HRID 1919265Notes

Reaction equation

HRID 1919265 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)=[CH:5][CH:4]=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C1C=[N+:30]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.P([O-])([O-])([O-])=O.N[C@H](C(O)=O)C.CC1N=CC(COP(O)(O)=O)=C(C=O)C=1O.[OH-].[Na+].COC1C=C2C(CCC(N)C2)=CC=1>O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C@H:9]([NH2:30])[CH2:10]2)=[CH:5][CH:4]=1

Participants

10

Reactant 8

HCID 1051Pyridoxal 5'-phosphateHCID 1061PhosphateHCID 5893Nadide (JAN/USAN/INN)HCID 5950L-AlanineHCID 14798Sodium HydroxideHCID 777857-Methoxy-2-tetraloneHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 116080152-Amino-7-methoxytetralin4×

Product 1

HCID 11008478(S)-7-methoxy-2-aminotetraline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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.

Workup

  1. additionwere poured
  2. additionwas added so that total volume was 30 ml
  3. customproduced in the reaction liquid
  4. customwas produced

Sources & evidence

ORD record
ord-ab1f590af9384582b9d32b85d5237c0b
Source dataset
uspto-grants-2012_05
Patent number
US08168412B2

Reaction notes

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