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1 ighly Stereoselective Reductions of α-alkyl-1,3-diketones and α- Alkyl-β-keto esters Catalyzed by Isolated NADP-dependent Ketoreductases Dimitris Kalaitzakis, a David J. Rozzell b, Spiros Kambourakis *b and Ioulia Smonou* a a Department of Chemistry, University of Crete, Iraklio 7149, Crete, Greece and b BioCatalytics Inc, 129 North ill Ave, Suite 13, Pasadena, CA 9116, USA Supporting Information Experimental Section General Considerations a-alkyl-1,3-diones 1-6 were prepared from commercially available 2,4-pentadione (acetylacetone) by alkylation with the proper alkyl halide. a-alkyl-β-keto esters 7, 8, were prepared from commercially available ethyl acetoacetate by alkylation with the proper alkyl halide. Racemic keto alcohols were prepared from pentan-2-one by aldol condensation with the corresponding aldehyde. Flash chromatography was carried out with 6 Å silica gel according to the procedure of Still (Still, W. C.; Kahn, M.; Mitra, A. J. rg. Chem. 1978, 14, ). The progress of the enzymatic reactions and the selectivities were determined by gas chromatography (P589II gas chromatograph equipped with an FID detector; column: 3m x.25mm x.25µm chiral capillary column, 2% permethylated cyclodextrin). MS were taken on a GC-MS (Simatzu GCMS-QP55 equipped with a S1

2 SPB-5 column and CI mass detector). 1 NMR and 13 C NMR spectra were recorded on a 3 Mz Bruker spectrometers in CDCl 3 solutions, by using Me 4 Si as internal standard. Chemical shifts are reported in ppm downfield from Me 4 Si. Yields refer to isolated and spectroscopically pure materials. Enzymatic Reductions Twenty different ketoreductases (KRED-11-12; BioCatalytics, Inc. Pasadena, CA USA) were screened to determine the best enzymes for the selective reduction of substrates methyl-2,4-pentanedione was used as the standard substrate. In addition to the ketoreductases, both NADP and glucose dehydrogenase (GLD) are products available from BioCatalytics. The screening was based in small-scale reactions (1 ml) where each substrate (25 mm) was mixed with NADP (2.5 mm, 2 mg), each ketoreductase (2 mg/ml), glucose (1 mm, 18 mg), glucose dehydrogenase (GLD, 2 mg/ml) for cofactor recycling, NaCl (1 mm, 6 mg) and sodium phosphate buffer (1 ml, 2 mm, p 6.9). The reactions were incubated at 37 ºC and reaction aliquots were taken every one hour and after extraction with ethyl acetate they were analyzed by GC chromatography. All the small-scale enzymatic reductions were accomplished according to the above screening reactions except for 3-methyl-2,4-pentanedione and 3-methyl-2,4-hexanedione which were reduced in p 6.5 and the reactions were completed in 24 hours. Larger-scale enzymatic reductions were prepared according to the following protocol. A phosphate-buffered solution (1 ml, p 6.9, 2 mm) containing 5 mm substrate, NaCl (2 mm), glucose (12 mm), NADP (.5 mm), glucose S2

3 dehydrogenase (5 mg) and the appropriate ketoreductase (5 mg) was stirred at 37 ºC for 24 hours, until GC analysis of crude extracts showed complete reaction. Periodically the p was readjusted to 6.9 with Na (2 M). Product was isolated by extracting the crude reaction mixture with EtAc (7 ml x 2). Sometimes centrifugation (6 rpm, 1 min) was required for the aqueous and the organic layers to separate as clear solutions. The combined organic layers were then extracted with saturated NaCl solution, dried over MgS 4 and evaporated to dryness. Pure, optically active alcohols were obtained in 9% to 91 % yield. The products were analyzed by NMR spectroscopy. Their optical purity was determined by chiral GC chromatography using 2% permethylated cyclodextrin column. According to this protocol diketone 1 (57 mg, 5 mm) was reduced with KRED12. Isolated yield 513 mg, 9%. 1 NMR: Ketoester 7 (72 mg, 5 mm) was reduced also with KRED12. Isolated yield 656 mg, 91%. Preparation of MPA-esters To a solution of the corresponding alcohol (.1 mmol) in dry C 2 Cl 2 were added 1.1 equiv. of DCC (.11 mmol) and 1.1 eqiv. f the corresponding (R) or (S) MPA (.11 mmol) and the reaction mixture was stirred at o C for 4-6 hr. After completion of the reaction the produced urea was filtered, the filtrate was evaporated and then chromatographed with 5/1 ex/etac and the produced corresponding MPA-ester was isolated. S3

4 Analytical and Spectral Data 1) GC analysis of racemic keto alcohol-1 with chiral capillary column, 2% permethylated cyclodextrin Sig. 1 in C:\PCEM\...\KALAITZ\123.D Time (min.) S4

5 2) 1 NMR (3 Mz, CDCl 3 ) of the racemic keto alcohol S5

6 3) GC analysis of the product, after enzymatic reduction of diketone-1 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\122.D Time (min.) S6

7 4) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-1 after enzymatic reduction with KRED S7

8 5) GC analysis of racemic keto alcohol-2 with chiral capillary column, 2% permethylated cyclodextrin Sig. 1 in C:\PCEM\...\KALAITZ\144.D Time (min.) S8

9 6) 1 NMR (3 Mz, CDCl 3 ) of the racemic keto alcohol S9

10 7) GC analysis of the product, after enzymatic reduction of diketone-2 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\145.D Time (min.) S1

11 8) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-2 after enzymatic reduction with KRED S11

12 9) GC analysis of the product, after enzymatic reduction of diketone-2 with KRED17 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\1262.D Time (min.) S12

13 1) GC analysis of the product, after enzymatic reduction of diketone-2 with KRED118 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\626.D Time (min.) S13

14 11) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-2 after enzymatic reduction with KRED S14

15 12) GC analysis of racemic keto alcohol-3 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\452.D Time (min.) S15

16 13) 1 NMR (3 Mz, CDCl 3 ) of racemic keto alcohol S16

17 14) GC analysis of the product, after enzymatic reduction of diketone-3 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\451.D Time (min.) S17

18 15) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-3 after enzymatic reduction with KRED S18

19 16) GC analysis of the product, after enzymatic reduction of diketone-3 with KRED114 (chiral capillary column, 2% permethylated cyclodextrin) 1.6e4 1.4e4 1.2e4 1.e Sig. 1 in C:\PCEM\...\KALAITZ\125.D Time (min.) S19

20 17) GC analysis of racemic keto alcohol-4 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\1167.D Time (min.) S2

21 18) 1 NMR (3 Mz, CDCl 3 ) of racemic keto alcohol S21

22 19) GC analysis of the product, after enzymatic reduction of diketone-4 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\416.D Time (min.) S22

23 2) GC analysis of the product, after enzymatic reduction of diketone-4 with KRED17 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\1182.D Time (min.) S23

24 21) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-4 after enzymatic reduction with KRED S24

25 22) GC analysis of the product, after enzymatic reduction of diketone-4 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) 2.e4 1.8e4 1.6e4 1.4e4 1.2e4 1.e Sig. 1 in C:\PCEM\...\KALAITZ\124.D Time (min.) S25

26 23) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-4 after enzymatic reduction with KRED S26

27 24) GC analysis of racemic keto alcohol-5 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\223.D Time (min.) S27

28 25) 1 NMR (3 Mz, CDCl 3 ) of racemic keto alcohol S28

29 26) GC analysis of the product, after enzymatic reduction of diketone-5 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\228.D Time (min.) S29

30 27) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-5 after enzymatic reduction with KRED S3

31 28) GC analysis of the product, after enzymatic reduction of diketone-5 with KRED17 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\735.D Time (min.) S31

32 29) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-5 after enzymatic reduction with KRED S32

33 3) GC analysis of the product, after enzymatic reduction of diketone-5 with KRED119 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\1199.D Time (min.) S33

34 31) 1 NMR (5 Mz, CDCl 3 ) of the produced keto alcohol-5 after enzymatic reduction with KRED S34

35 32) GC analysis of racemic keto alcohol-6 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\161.D Time (min.) S35

36 33) 1 NMR (3 Mz, CDCl 3 ) of racemic keto alcohol S36

37 34) GC analysis of the product, after enzymatic reduction of diketone-6 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\166.D Time (min.) S37

38 35) 1 NMR (3 Mz, CDCl 3 ) of the produced keto alcohol-6 after enzymatic reduction with KRED S38

39 36) GC analysis of racemic hydroxy ester-7 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\316.D Time (min.) S39

40 37) 1 NMR (3 Mz, CDCl 3 ) of racemic hydroxy ester S4

41 38) GC analysis of the product, after enzymatic reduction of keto ester-7 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\322.D Time (min.) S41

42 39) 1 NMR (3 Mz, CDCl 3 ) of the produced hydroxy ester-7 after enzymatic reduction with KRED S42

43 4) GC analysis of the product, after enzymatic reduction of keto ester-7 with KRED17 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\338.D Time (min.) S43

44 41) 1 NMR (3 Mz, CDCl 3 ) of the produced hydroxy ester-7 after enzymatic reduction with KRED S44

45 42) GC analysis of racemic hydroxy ester-78(chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\326.D Time (min.) S45

46 43) 1 NMR (3 Mz, CDCl 3 ) of racemic hydroxy ester S46

47 44) GC analysis of the product, after enzymatic reduction of keto ester-8 with KRED12 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\33.D Time (min.) S47

48 45) 1 NMR (3 Mz, CDCl 3 ) of the produced hydroxy ester-8 after enzymatic reduction with KRED S48

49 46) GC analysis of the product, after enzymatic reduction of keto ester-8 with KRED116 (chiral capillary column, 2% permethylated cyclodextrin) Sig. 1 in C:\PCEM\...\KALAITZ\58.D Time (min.) S49

50 47) 1 NMR (5 Mz, CDCl 3 ) of the produced hydroxy ester-8 after enzymatic reduction with KRED S5

51 Determination of absolute configuration of hydroxy compounds* MPA R 1 Me R 2 δ RS < δ RS > R 2 R 1 S Me Me R 1 Me R R 2 1 R R 2 2 R 1 or R2 R 1 Syn Me R 1 Me R R R R 1 R 1 or R2 R 1 Anti J vic (anti) > J vic (syn) *Seco, J. M.; Quinoa, E.; Riguera, R. Chem. Rev. 24, 14, Stiles, M.; Winkler, R. R.; Chang, Y.-L.; Traynor, L. J. Am. Chem. Soc.1964, 86, ouse,..; Crumrine, D. S.; Teranishi, A. Y.; lmstead,. D. J. Am. Chem. Soc.1973, 95, S51

52 48) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-1 produced after enzymatic reduction with KRED From 12 Me C C (R) S52

53 49) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-1 produced after enzymatic reduction with KRED From 12 Me C C (S) S53

54 5) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-2 produced after enzymatic reduction with KRED12 5 From 12 Me C C (R) From 12 Me C C (R) S

55 51) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-2 produced after enzymatic reduction with KRED From 12 Me C C (S) From 12 Me C C (S) S

56 52) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-2 produced after enzymatic reduction with KRED From 118 Me C C (R) From 118 Me C C (R) S

57 53) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-2 produced after enzymatic reduction with KRED From 118 Me C C (S) From 118 Me C C (S) S57

58 54) 1 NMR (5 Mz, CDCl 3 ) of keto alcohol-2 produced after enzymatic reduction with KRED12 (decoupling at 1.2ppm) From J vic (syn) = 4,9 z S58

59 55) 1 NMR (5 Mz, CDCl 3 ) of keto alcohol-2 produced after enzymatic reduction with KRED118 (decoupling at 1.24ppm) From J vic (anti) = 6.7 z S59

60 56) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-4 produced after enzymatic reduction with KRED From 12 Me C C (R) From 12 Me C C (R) S

61 57) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-4 produced after enzymatic reduction with KRED12 25 From 12 Me C C (S) From 12 Me C C (S) S

62 58) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-4 produced after enzymatic reduction with KRED From 12 Me C C (R) From 12 Me C C (R) S

63 59) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-4 produced after enzymatic reduction with KRED12 From 12 Me C C (S) From 12 Me C C (S) S

64 6) 1 NMR (5 Mz, CDCl 3 ) of keto alcohol-4 produced after enzymatic reduction with KRED12 (decoupling at 1.21ppm) From J vic (syn) = 4.7 z S64

65 61) 1 NMR (5 Mz, CDCl 3 ) of keto alcohol-4 produced after enzymatic reduction with KRED12 (decoupling at 1.25ppm) From J vic (anti) = 6.4 z S65

66 62) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-5 produced after enzymatic reduction with KRED12 3 From 12 Me C C (R) From 12 Me C C (R) S

67 63) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-5 produced after enzymatic reduction with KRED12 4 From 12 Me C C (S) From 12 Me C C (S) S

68 64) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-5 produced after enzymatic reduction with KRED From 119 Me C C (R) From 119 Me C C (R) S

69 65) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-5 produced after enzymatic reduction with KRED From 119 Me C C (S) From 119 Me C C (S) S

70 66) 1 NMR (5 Mz, CDCl 3 ) of keto alcohol-5 produced after enzymatic reduction with KRED12 (decoupling at 1.2ppm) From J vic (syn) = 4.5 z S7

71 67) 1 NMR (5 Mz, CDCl 3 ) of keto alcohol-5 produced after enzymatic reduction with KRED119 (decoupling at 1.24ppm) From J vic (anti) = 6.3 z S71

72 68) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of keto alcohol-6 produced after enzymatic reduction with KRED From 12 Me C C (R) From 12 Me C C (R) S

73 69) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of keto alcohol-6 produced after enzymatic reduction with KRED From 12 Me C C (S) From 12 Me C C (S) S

74 7) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of hydroxy ester-7 produced after enzymatic reduction with KRED From 12 Me C C (R) From 12 Me C C (R) S

75 71) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of hydroxy ester-7 produced after enzymatic reduction with KRED12 4 From 12 Me C C (S) From 12 Me C C (S) S

76 72) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of hydroxy ester-7 produced after enzymatic reduction with KRED From 17 Me C C (R) From 17 Me C C (R) S

77 73) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of hydroxy ester-7 produced after enzymatic reduction with KRED17 1 From 17 Me C C (S) From 17 Me C C (S) S

78 74) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of hydroxy ester-8 produced after enzymatic reduction with KRED From 12 Me C C (R) From 12 Me C C (R) S78 1..

79 75) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of hydroxy ester-8 produced after enzymatic reduction with KRED From 12 Me C C (S) From 12 Me C C (S) S

80 76) 1 NMR (3 Mz, CDCl 3 ) of the (R)-MPA ester of hydroxy ester-8 produced after enzymatic reduction with KRED From 116 Me C C (R) From 116 Me C C (R) S

81 77) 1 NMR (3 Mz, CDCl 3 ) of the (S)-MPA ester of hydroxy ester-8 produced after enzymatic reduction with KRED116 2 From 116 Me C C (S) From 116 Me C C (S) S81 1..

82 78) 1 NMR (5 Mz, CDCl 3 ) of hydroxy ester-8 produced after enzymatic reduction with KRED12 (decoupling at 1.21ppm) From J vic (syn) = 5 z S82

83 79) 1 NMR (5 Mz, CDCl 3 ) of hydroxy ester-8 produced after enzymatic reduction with KRED116 (decoupling at 1.24ppm) From J vic (anti) = 6 z S83

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