Sodium Chloride → HCID 12567691, compound

HRID 1594431Notes

Reaction equation

HRID 1594431 reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[Na+].C1C=[N+]([C@@H]2[O:21][C@H:20](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:19](O)[C@H]2O)C=C(C(N)=O)C=1.[O:59]=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[CH2:71]([O:73][C:74](=[O:91])[CH:75]([CH2:84][C:85]1[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=1)[C:76](=[O:83])[CH2:77]C(OCC)=O)[CH3:72]>>[CH2:20]([O:21][C:77](=[O:59])[CH:76]([OH:83])[CH:75]([CH2:84][C:85]1[CH:86]=[CH:87][CH:88]=[CH:89][CH:90]=1)[C:74]([O:73][CH2:71][CH3:72])=[O:91])[CH3:19]

Participants

6

Reactant 5

HCID 5234Sodium ChlorideHCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 62657Potassium Phosphate, TribasicHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×HCID 12200242Diethyl 2-benzyl-3-oxopentanedioate

Product 1

HCID 12567691HCID 12567691, compound

Procedure

The procedure of Example 4 was repeated for the screening of the KRED-8000 kit with 3-benzyloxaloacetate diethyl ester. Enzymes KRED 1008 and KRED 1004 showed complete reduction to the alcohol. Both reactions were repeated in larger scale for the purpose of isolating the product and verifying the structure using 1H NMR spectroscopy. In 20 mL of an aqueous solution containing 250 mM potassium phosphate (pH 6.7), 5% (v/v) polyethelene glycol (MW 1450) 0.5 M sodium chloride, 0.076 g of NADP+, 3.5 g of D-glucose 0.1 g of both lyophilized enzymes glucose dehydrogenase and KRED 1004 or KRED 1008 0.5 g of 3-benzyloxaloacetate diethyl ester were added. The reactions were incubated at 37° C. in a shake oven for 20 h before they were extracted with ethyl acetate. The organic layers were evaporated to dryness, and the alcohols were further purified using silica gel chromatography, before they were analyzed by 1H NMR. Both enzymes gave 2-hydroxy-3-benzylsuccinate diethyl ester as the only product.

Workup

  1. customof isolating the product
  2. additionwere added
  3. extractionwere extracted with ethyl acetate
  4. customThe organic layers were evaporated to dryness
  5. customthe alcohols were further purified

Sources & evidence

ORD record
ord-532cb2af9f7846479ad36b1f120ebf67
Source dataset
uspto-grants-2007_11
Patent number
US07301031B2

Reaction notes

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