NADPH → Ethyl 3-hydroxy-3-(thiophen-2-yl)propanoate

HRID 1443321Notes

Reaction equation

HRID 1443321 reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[CH2:13]([O:15][C:16](=[O:25])[CH2:17][C:18](=[O:24])[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH3:14].C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3O)C=2N=1.C1N=C(N)C2N=CN([C@@H]3O[C@H](COP(OP(OC[C@H]4O[C@@H](N5C=C(C(N)=O)CC=C5)[C@H](O)[C@@H]4O)(O)=O)(O)=O)[C@@H](O)[C@H]3OP(O)(O)=O)C=2N=1.C(O)C(N)(CO)CO.Cl>CC(O)C>[CH2:13]([O:15][C:16](=[O:25])[CH2:17][CH:18]([OH:24])[C:19]1[S:20][CH:21]=[CH:22][CH:23]=1)[CH3:14]

Participants

7

Reactant 5

HCID 5884NADPHHCID 93573Tromethamine hydrochlorideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×HCID 255159Ethyl 3-oxo-3-(thiophen-2-yl)propanoate2×HCID 439153Nadh

Product 1

HCID 11252640Ethyl 3-hydroxy-3-(thiophen-2-yl)propanoate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

An aqueous solution comprising a composition of 2% glucose, 1% yeast extract, 1% polypeptone, and 0.6% malt extract was used as the medium, and Filobasidium uniguttulatum IFO 0699 was inoculated into this and aerobically cultured at 28° C. for 24 hours. After completion of the culturing, the culture medium (1 ml) was collected and centrifuged to isolate the cells. 3-Oxo-3-(2-thienyl)propionic acid ethyl ester to be used as the substrate was synthesized in accordance with the method described in EP-A-751427. Said cells were suspended in 200 μl of a reaction solution comprising 100 mM glucose, 0.24% 3-oxo-3-(2-thienyl)propionic acid ethyl ester, 0.01% NADH, 0.01% NADPH and 100 mM Tris-HCl buffer (pH 7.5) and allowed to undergo the reaction at 30° C. on a shaker. After 18 hours of the commencement of the reaction, 800 μl of 2-propanol was added thereto, the cells were removed by centrifugation, and then a sample of the supernatant was analyzed by HPLC. The analysis was carried out under the following conditions using Chiralpak AD-RH (mfd. by Daicel) as the HPLC column.

Workup

  1. extractionextract
  2. extraction1% polypeptone, and 0.6% malt extract
  3. customAfter completion of the culturing, the culture medium (1 ml) was collected
  4. customto isolate the cells
  5. customwas synthesized in accordance with the method
  6. customthe reaction at 30° C. on a shaker
  7. additionwas added
  8. customthe cells were removed by centrifugation

Sources & evidence

ORD record
ord-2d62d9b326de48809eb241fe655f5c19
Source dataset
uspto-grants-2010_02
Patent number
US07659409B2

Reaction notes

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