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

HRID 1919267Notes

Reaction equation

HRID 1919267 reaction equation
COC1C=C2C(CCC(=O)C2)=CC=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.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.[OH-].[Na+].[CH3:94][O:95][C:96]1[CH:105]=[C:104]2[C:99]([CH2:100][CH2:101][CH:102]([NH2:106])[CH2:103]2)=[CH:98][CH:97]=1>>[CH3:94][O:95][C:96]1[CH:105]=[C:104]2[C:99]([CH2:100][CH2:101][C@H:102]([NH2:106])[CH2:103]2)=[CH:98][CH:97]=1

Participants

8

Reactant 7

HCID 1051Pyridoxal 5'-phosphateHCID 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-methoxytetralin2×

Product 1

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

Procedure

To 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 (pNMTA, pSTVPAG), obtained in Example 9, which expresses MTA, PALDH, and GDH 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. The rate of conversion into 7-methoxy-2-aminotetraline after the reaction was 60.2%. The absolute configuration of 7-methoxy-2-aminotetraline was (S), and the optical purity was 97.1% e.e.

Workup

  1. custom(pNMTA, pSTVPAG), obtained in Example 9, which
  2. additionwas added so that total volume was 30 ml

Sources & evidence

ORD record
ord-335422b31c2c480089af6e84206884fc
Source dataset
uspto-grants-2012_05
Patent number
US08168412B2

Reaction notes

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