Stereoselective enzymatic reduction of keto-salinosporamide to (-)-salinosporamide A (NPI-0052)

Tetrahedron Letters

Volumn 48, Issue 14, 2007, Pages 2537-2540

  Manam, Rama Rao ^a   Macherla, Venkat R ^a   Potts, Barbara C M ^a  

^a Nereus Pharmaceuticals Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; KETO SALINOSPORAMIDE; KETONE; NPI 0052; PROTEASOME INHIBITOR; SALINOSPORAMIDE A; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; DIASTEREOISOMER; ENZYME ACTIVITY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 33847686427     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.02.017     Document Type: Article

References (13)

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11. Protocol for small scale enzymatic reduction: Keto-salinosporamide (2, 10 mM in DMSO) was mixed with NAD+ (2 mM), ketoreductase (10 mg/mL, KRED-EXP-C1A or KRED-EXP-B1Y), sodium formate (20 mM), FDH-101 (2 mg/mL) for cofactor recycling, and sodium phosphate buffer (1 mL, 150 mM, pH 6.9). The reaction mixtures were incubated at 33 °C for an hour, extracted with ethyl acetate, evaporated to dryness in a speed vacuum, redissolved in acetonitrile, and analyzed by HPLC for product formation.
12. Denora, N.; Potts, B. C. M.; Stella, V. J. J. Pharm. Sci., in press.
13. 13C NMR spectra with those of an authentic sample. Ketoreductases KRED-EXP-C1A and KRED-EXP-B1Y, GDH-103, d-glucose, and NAD grade II free acid were obtained from BioCatalytics, Pasadena, CA.