Phosphate → Ethyl 2-hydroxycyclopentanecarboxylate

HRID 1586647Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586647
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].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.P([O-])([O-])([O-])=O.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](OP(O)(O)=O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1>>[OH:1][CH:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

6

Edukt 5

HCID 1061PhosphateHCID 5884NADPHHCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 69136Ethyl 2-oxocyclopentanecarboxylate2×HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal3×

Produkt 1

HCID 275611Ethyl 2-hydroxycyclopentanecarboxylate

Versuchsvorschrift

The asymmetric reduction of ethyl 2-oxocyclopentanecarboxylate was carried out by using this reductase (1). Namely, 4 ml of the reaction mixture containing the reductase (1) (2U), NADPH (0.8 μmol), ethyl 2-oxocyclopentanecarboxylate (100 μmol, 16 mg), phosphate buffer solution (pH 7.0, 400 μmol), glucose dehydrogenase [manufactured by Sigma, Co., U.S.A.; 2U (wherein 1U is defined as the amount of the enzyme which reduces 1 μmol of NADP+ per 1 minute in the presence of glucose)] and glucose (100 μmol) was incubated at 30° C. with gentle shaking to promote the enzymatic reaction. After 6 hour-incubation, the reaction mixture was extracted according to the same manner as in Example 3. The extract was analyzed by gas chromatography described in Example 1. As a result, the yield of the cis isomer was 15.9 mg (reduction yield >99%), and neither the remaining substrate nor the trans isomer was detected. On the other hand, the extract above was distilled off according to the the same manner as in Example 3 to obtain the reduction product, ethyl 2-hydroxycyclopentane-carboxylate. The resulting reduction product was analyzed by high performance liquid chromatography as described in Example 1. As a result, only the cis 2 isomer was detected and no other isomers were detected.

Aufarbeitung

  1. customper 1 minute
  2. customwas incubated at 30° C.
  3. customthe enzymatic reaction
  4. extractionthe reaction mixture was extracted
  5. extractionOn the other hand, the extract
  6. distillationabove was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-980771627a7b408582d974db79e9a5c9
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05215919

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