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

HRID 1919266노트

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HRID 1919266 반응식
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

참가 물질

8

반응물 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-methoxytetralin2회

생성물 1

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

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-a2ceb9471f53409da87cfdeae32e1271
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168412B2

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