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

HRID 1919276Notes

Reaction equation

HRID 1919276 reaction equation
COC1C=C2C(CCC(=O)C2)=CC=1.C([O-])=O.[Na+].C1C=[N+]([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.N[C@H](C(O)=O)C.CC1N=CC(COP(O)(O)=O)=C(C=O)C=1O.[CH3:84][O:85][C:86]1[CH:95]=[C:94]2[C:89]([CH2:90][CH2:91][CH:92]([NH2:96])[CH2:93]2)=[CH:88][CH:87]=1>C(O)=O>[CH3:84][O:85][C:86]1[CH:95]=[C:94]2[C:89]([CH2:90][CH2:91][C@H:92]([NH2:96])[CH2:93]2)=[CH:88][CH:87]=1

Participants

8

Reactant 6

HCID 1051Pyridoxal 5'-phosphateHCID 5893Nadide (JAN/USAN/INN)HCID 5950L-AlanineHCID 777857-Methoxy-2-tetraloneHCID 2723810Sodium FormateHCID 116080152-Amino-7-methoxytetralin2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

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.

Workup

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

Sources & evidence

ORD record
ord-9290007c1ef24d2dbccd522bdcf1846c
Source dataset
uspto-grants-2012_05
Patent number
US08168412B2

Reaction notes

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