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- Ἔβέρ Παπαϊωάννου
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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Supplementary Information Immobilization of Pseudomonas fluorescens lipase on silk fibroin spheres: An alternative protocol for the enantioselective synthesis of halohydrins Irlon M. Ferreira, a,b Sergio A. Yoshioka, c João V. Comasseto d,e and André L. M. Porto a * a Laboratório de Química Orgânica e Biocatálise, Instituto de Química de São Carlos, Universidade de São Paulo, Av. João agnone, Ed. Química Ambiental, J. Santa Angelina, 1100, São Carlos, São Paulo, Brazil. almporto@iqsc.usp.br. b Universidade Federal do Amapá, Grupo de Biocatálise e Biotransformação em Química Orgânica, Rod. Juscelino Kubitscheck, KM 02, S/N J. Marco Zero, , Macapá, AP, Brazil. c Laboratório de Bioquímica e Biomateriais, Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador São-Carlense, 400, São Carlos, SP, Brazil. d Instituto de Química, Universidade de São Paulo, Av. Professor Lineu Prestes 748, São Paulo, SP, Brazil. e Instituto de Ciências Ambientais, Químicas e Farmacêuticas,Universidade Federal de São Paulo, Av. Prof. Artur Riedel, 275, iadema, SP, Brazil. S1
2 Table of contents 1. Optical rotations of the products obtained from of P. fluorescens lipase on silk fibroin spheres....s1 2. Thermogravimetric curves of samples: (--) Silk fibroin sphere; ( ) Immobilized lipase on silk fibroin sphere.s H, 13 C NMR and Mass Spectral data... S5-S8 4. Copies of 1 H and 13 C NMR Spectra......S9-S20 4. GC-FI Chromatograms....S9-S20 5. References S44 S2
3 Optical rotations of the products obtained from of P. fluorescens lipase on silk fibroin spheres. Compounds α] T Experimental α] T Literature 26 (R)-1a ] (c 1.0, CHCl 3 ) a 20 ] (c 1.0, CHCl 3 ) 1 26 (R)-1b ] (c 0.8, CHCl 3 ) a 20 ] - 39,5 (c 0.5, CHCl 3 ) 2 26 (R)-1c ] (c 1.0, CHCl 3 ) a 20 ] (c 2.85, CHCl 3 ) 3 26 (R)-1d ] (c 1.1, CHCl 3 ) a 20 ] (c 1.0, CHCl 3 ) 1 26 (S)-2a ] (c 1.5, CHCl 3 ) a 20 ] (c1.0, EtOAc) 4 26 (S)-2b ] (c 0.5, CHCl 3 ) a - 26 (S)-2c ] (c 2, CHCl 3 ) a 25 ] (c 3.4, CHCl 3 ) 3 26 (S)-2d ] (c 1.0, CHCl 3 ) a 25 ] (c1.15, CHCl 3 ) 5 26 (S)-3a ] (c 0.4, CHCl 3 ) a 24 ] (c 1.0, CHCl 3 ) 6 26 (S)-3b ] (c 0.6, CHCl 3 ) a 24 ] (c 1.0, CHCl 3 ) 6 25 (S)-3c ] (c 0.6, CHCl 3 ) a 24 ] (c 1.0, CHCl 3 ) 6 25 (S)-4 ] +2.5 (c 0.4, CHCl 3 ) b - a The optical rotation was measured in CHCl 3 on a Perkin-Elmer 241 polarimeter equipped with a lamp Na-589nm. b The optical rotation was measured on a JASCO in CHCl 3 P2000 polarimeter equipped with a 589nm-lamp Na. S3
4 TG (% / 0 C) TG (% / 0 C) Thermogravimetric curves of samples: (--) Silk fibroin sphere; ( ) Immobilized lipase on silk fibroin sphere. 0,0 A B 0,4 A B 0,2 0,4 0,6 0,6 0, Temperature Temperatura ( 0 C) 0, C C Temperature Temperatura ( 0 C) S4
5 2-chloro-1-phenylethanol (1a): C 8 H 9 ClO, g.mol -1. Yellow oil; 1 H NMR (400 MHz, CCl 3 ppm) δ: 3.71 (dd, J = 11.7 and 4.6 Hz, 1H), 3.78 (dd, J = 11.7 and 8.0 Hz, 1H), 5.95 (dd, J = 8.0 and 4.6 Hz, 1H), (m, 5H); 13 C NMR (100 MHz, CCl 3 ) δ (ppm): 50.9, 74, 126, 128.4, 128.6, 139.9; MS (EI, 70 ev) m/z (%): 156 (11), 107 (100), 79 (77), 51 (17); IR νmax (cm -1 ): 3404, 2956, 1494, 1064, bromo-1-phenylethanol (1b): C 8 H 9 BrO, g.mol -1. Yellow oil; 1 H NMR (400 MHz, CCl 3 ppm) δ: 1.57 (s, 1H), 3.48 (dd, J = 10.5 and 8.8 Hz, 1H), 3.60 (dd, J = 10.5 and 3.4 Hz, 1H), 4.89 (dd, J = 8.8 and 3.2 Hz, 1H), (m, 5H); 13 C NMR (100 MHz, CCl 3 ppm) δ: 39.9, 73.1, 127.3, 128.8, 134.2, 138.7; MS (EI, 70 ev) m/z (%): 200 (4), 107 (100), 79 (28), 51 (12); IR νmax (cm -1 ): 3398, 2954, 2926, 1429, 1454, 1377, 1068, bromo-1-(4-bromophenyl)ethanol (1c): C 8 H 8 Br 2 O, g.mol -1. White solid, m.p.: 59 ºC (lit ); 1 H NMR (400 MHz, CCl 3 ppm) δ: 3.49 (dd, J = 10.8 Hz, 1H), 3.61 (dd, J = 10.5, 4 Hz, 1H), 4.91 (m, 1H), 7.27 (d, J = 8 Hz), 7.51 (d, J = 8 Hz); 13 C NMR (100 MHz, CCl 3 ppm) δ: 39.9, 73, 122.3, 127.6, 131.7, 139.2; MS (EI, 70 ev) m/z (%): 280 (8), 185 (100), 157 (23), 77 (75), 51 (20); IR max (cm -1 ): 3398, 2954, 2926, 1492, 1454, 1068, 759, 700. S5
6 2-bromo-1-(4-chlorophenyl)etanol (1d): C 8 H 8 BrClO, g.mol -1. White solid, m.p.: 59 ºC (lit ºC); 1 H NMR (400 MHz, CCl 3 ppm) δ: 3.50 (dd, J = 10.4 and 8.8 Hz, 1H), 3.61 (dd, J = 10.5 and 3.4 Hz, 1H), 4.91 (dt, J = 8.6 and 3.1, 1H), (m, 4H); 13 C NMR (100 MHz, CCl 3 ppm) δ: 138.7, 128.8, 127.3, 126.8, 73.0, 39.9; MS (EI, 70 ev) m/z (%): 236 (6), 141 (100), 113 (20), 77 (54), 51 (8); IR max (cm -1 ): 3390, 2960, 2865, 1597, 1429, 1091, 833, 727, chloro-1-phenylethyl acetate (2a): C 10 H 11 ClO 2, 198,04 g.mol -1. White solid, m.p.: 47 ºC; 1 H NMR (500 MHz, CCl 3 ppm) δ: 3,71 (dd, J = 11,7 and 4,6 Hz, 1 H), 3,78 (dd, J = 11,7 and 8 Hz, 1 H), 5,95 (dd, J = 8,4 and 4,9 Hz, 1 H), 7,48-7,30 (m, 5 H) ppm; 13 C NMR (125 MHz, CCl 3 ppm) δ: 20,98, 46,50, 75,0, 126,6, 128,7, 128,8, 137,1, 169,8; MS (EI, 70 ev) m/z (%):198 (3), 162 (15), 102 (12), 77 (23), 43 (100); IR max (cm -1 ): 2960, 2929, 1747, 1373, 1230, 1024, 761, bromo-1-phenylethyl acetate (2b): C 10 H 11 BrO 2, g.mol -1. Colorless oil; 1 H NMR (500 MHz, CCl 3 ppm) δ: (m, 1H), 5.05 (dd, J = 7.5 and 6.2 Hz, 1H), (m, 2H), 2.05 (s, 3H); 13 C NMR (125 MHz, CCl 3 ) δ (ppm): 169.7, 136.6, 131.9, 128.3, 122.9, 74.1, 33.7, 20.9; MS (EI, 70 ev) m/z (%): 242 (8), 198 (16), 141 (32), 103 (36), 77 (78), 40 (100); IR max (cm -1 ): 2964, 1745, 1489, 1236, 758. S6
7 2-bromo-1-(4-bromophenyl)ethyl acetate (2c): C 10 H 10 Br 2 O 2, g.mol -1. Colorless oil; 1 H NMR (400 MHz, CCl 3 ) δ (ppm): 7.49 (d, J = 8.5 Hz, 2H), (m, 2H), 5.90 (dd, J = 7.6 and 5.1 Hz, 1H), 3.60 (dd, J = 10.8 and 7.7 Hz, 1H), 3.54 (dd, J = 10.8 and 5.1 Hz, 1H), 2.12 (s, 3H); 13 C NMR (100 MHz, CCl 3 ) δ (ppm): 169.7, 136.6, 131.9, 128.3, 122.9, 74.1, 33.7, 20.9; MS (EI, 70 ev) m/z (%): 322 (0.3), 242 (15), 200 (31), 183 (26), 157 (6), 102 (21), 77 (23), 43 (100); IR max (cm -1 ): 2962, 2926, 1745, 1489, 1371, 1236, 1070, 1012, 821, bromo-1-(4-chlorophenyl)ethyl acetate (2d): C 10 H 10 BrClO 2, g.mol -1. Colorless oil; 1 H NMR (500 MHz, CCl 3 ppm) δ: 7.34 (d, J = 8.6 Hz, 2H), 7.28 (d, J = 8.6 Hz, 2H), 5.92 (dd, J = 7.7 and 5.0 Hz, 1H), 3.60 (dd, J = 10.8 and 7.7 Hz, 1H), 3.54 (dd, J = 10.8 and 5.0 Hz, 1H), 2.12 (d, J = 2.4 Hz, 3H); 13 C NMR (125 MHz, CCl 3 ppm) δ: , , , , , , 74.07, 33.83, 20.89; MS (IE, 70 ev) m/z (%): 278 (0.15), 196 (20), 154 (45), 137 (40), 103 (14), 77 (17), 43 (100); IR max (cm -1 ): 3032, 2964, 1745, 1492, 1373, 1238, 1091, phenyloxirane (3a): C 8 H 8 O, g.mol -1. Colorless oil; NMR 1 H (400 MHz, CCl 3 ppm) δ: 2,82 (dd, J = 5.5 and 2.6 Hz, 1H), 3.17 (dd, J = 5.5 and 4.1 Hz, 1H), 3.88 (dd, J = 4.0 and 2.6 Hz, 1H), (m, 5H); 13 C NMR (100 MHz, CCl 3 ) δ (ppm): (s), 128.5, 128.1, 125.5, 52.3, 51.1; MS (EI, 70 ev) m/z (%): 120 (43), 119 (67), 91 (100), 77 (10), 51 (20); IR max (cm -1 ): 2913, 1495, 1453, 876, 760. S7
8 2-(4-bromophenyl)oxirane (3b): C 8 H 7 BrO, g.mol -1. Colorless oil; 1 H NMR (400 MHz, CCl 3 ) δ (ppm): 2.75 (dd, J = 5.4 and 2.5 Hz, 1H); 3.14 (dd, J = 5.3 and 4.2 Hz, 1H), (m, 1H), 7.15 (d, J = 8.4 Hz, 2H), 7.47 (d, J = 8.4 Hz, 2H); 13 C NMR (100 MHz, CCl 3 ) δ (ppm): 51.2, 58.8, 122, 127, 131, 137; MS (EI, 70 ev) m/z (%): 198 (13), 169 (20), 119 (55), 89 (100), 77 (7), 63 (32); IR max (cm -1 ): 2958, 1745, 1517, 1230, (4-chlorophenyl)oxirane (3c): C 8 H 7 ClO, 154,07 g.mol -1. Colorless oil. 1 H NMR (400 MHz, CCl 3 ) δ (ppm): 7.30 (d, J = 8.5 Hz, 2H), 7.19 (d, J = 8.5 Hz, 2H), 3.82 (dd, J = 3.7 and 2.8 Hz, 1H), 3.13 (dd, J = 5.4 and 4.1 Hz, 1H), 2.73 (dd, J = 5.4 and 2.5 Hz, 1H) ppm; 13 C NMR (100 MHz, CCl 3 ) δ (ppm): 136.1, 133.9, 128.7, 126.8, 51.7, 51.2 ppm; MS (EI, 70 ev) m/z (%): 154 (23), 119 (69), 89 (100), 63 (20); IR max (cm -1 ): 2927, 2854, 1215, 759. (S)-1-(4-chlorophenyl)-2-(1H-1,2,3-triazol-1-yl)ethanol (4): C 11 H 11 ClN 2 O, g.mol -1. White solid, m.p.: ºC (lit ); 1 H NMR (400 MHz, C 3 O) δ (ppm): 4.14 (dd, J = 14.1 and 6,9 Hz, 1H), 4,21 (dd, J = 14,1 and 4,4 Hz, 1H), 7,46 (s, 1H), 4,91 (dd, J = 6,9 and 4,5 Hz, 1H), 7,03 (t, J = 1,3 Hz, 1H), 6,88 (s, 1H), 7,34-7,22 (m, 4H); 13 C NMR (100 MHz, C 3 O) δ (ppm): 141,8, 139, 134,5, 129,4, 128,7, 128,4, 121,5, 73,4, 55; MS (EI, 70 ev) m/z (%): 222 (5), 141 (19), 113 (13), 82 (100), 77 (40), 51 (7); IR max (cm -1 ) = 3116, 2929, 2856, 1514, 1408, 1072, 748, 661. S8
9 1 H NMR (500 MHz, CCl 3 ) of 2-chloro-1-phenylethanol (1a) 13 C NMR (125 MHz, CCl 3 ) of 2-chloro-1-phenylethanol (1a) S9
10 1 H NMR (400 MHz, CCl 3 ) of 2-bromo-1-phenylethanol (1b) 13 C NMR (100 MHz, CCl 3 ) of 2-bromo-1-phenylethanol (1b) S10
11 1 H NMR (400 MHz, CCl 3 ) of 2-bromo-1-(4-bromophenyl)ethanol (1c). 13 C NMR (100 MHz, CCl 3 ) of 2-bromo-1-(4-bromophenyl)ethanol (1c). S11
12 1 H NMR (400 MHz, CCl 3 ) of 2-bromo-1-(4-chlorophenyl)etanol (1d) Fig. S C NMR (100 MHz, CCl 3 ) of 2-bromo-1-(4-chlorophenyl)etanol (1d) S12
13 1 H NMR (500 MHz, CCl 3 ) of 2-chloro-1-phenylethyl acetate (2a). 13 C NMR (125 MHz, CCl 3 ) of 2-chloro-1-phenylethyl acetate (2a). S13
14 1 H NMR (500 MHz, CCl 3 ) of 2-bromo-1-phenylethyl acetate (2b). 13 C NMR (125 MHz, CCl 3 ) of 2-bromo-1-phenylethyl acetate (2b). S14
15 1 H NMR (400 MHz, CCl 3 ) of 2-bromo-1-(4-bromophenyl)ethyl acetate (2c). 13 C NMR (100 MHz, CCl 3 ) of 2-bromo-1-(4-bromophenyl)ethyl acetate 2c). S15
16 1 H NMR (400 MHz, CCl 3 ) of 2-bromo-1-(4-chlorophenyl)ethyl acetate (2d). 13 C NMR (100 MHz, CCl 3 ) of 2-bromo-1-(4-chlorophenyl)ethyl acetate (2d). S16
17 1 H NMR (400 MHz, CCl 3 ) of 2-phenyloxirane (3a) 13 C NMR (100 MHz, CCl 3 ) of 2-phenyloxirane (3a) S17
18 1 H NMR (400 MHz, CCl 3 ) of 2-(4-bromophenyl)oxirane (3b) 13 C NMR (100 MHz, CCl 3 ) of 2-(4-bromophenyl)oxirane (3b) S18
19 1 H NMR (400 MHz, CCl 3 ) of 2-(4-chlorophenyl)oxirane (3c) 13 C NMR (100 MHz, CCl 3 ) of 2-(4-chlorophenyl)oxirane (3c) S19
20 1 H NMR (400 MHz, C 3 O) of (S)-1-(4-chlorophenyl)-2-(1H-1,3-triazol-1-yl)ethanol (4) Fig. S C NMR (100 MHz, C 3 O) of (S)-1-(4-chlorophenyl)-2-(1H-1,3-triazol-1- yl)ethanol (4) S20
21 GC-FI Chromatograms: (A) Standard of (R,S)-2-chloro-1-phenylethanol 1a. (B) Standard of (R,S)-2-chloro-1-phenylethyl acetate 2a. (C) Kinetic resolution of (S)-2a and (R)-1a by lipase from C. cylindracea () R. niveus (E) A. niger (F) P. fluorescens after 24 h of reaction on 32 ºC, 130 rpm. A B C E F S21
22 GC-FI Chromatograms: Kinetic resolution of (S)-2b and (R)-1b by lipase from (A) P. fluorescens (B) C. cylindracea (C) R. niveus () A. niger after 24 h of reaction on 32 ºC, 130 rpm. (F) Standard of (R,S)-2-chloro-1-phenylethanol 1b (A) (B) (C) () (E) S22
23 GC-FI Chromatograms: Kinetic resolution of (R,S)-2a by FS-LPf in different concentrations (a) 50 mg (24h, 32ºC, 130 rpm); (b) 150 mg (24h, 32ºC, 130 rpm); (c) 100 mg (48h, 32ºC, 130 rpm). (A) (B) (C) S23
24 GC-FI Chromatograms: (A) Standard of (R,S)-1c. (B) Standard of acetate (R,S)-2c. (C) Kinetic resolution of (S)-2c and (R)-1c by FS-LPF after 24 h of reaction (32 ºC, 130 rpm) uv(x100,000) Chromatogram A C Column Temp.(Setting) min 5.0 uv(x10,000) Chromatogram B C Column Temp.(Setting) min 2.50 uv(x10,000) C Chromatogram Column Temp.(Setting) C min S24
25 GC-FI Chromatograms: Epoxide (S)-3a. GC-FI Chromatograms: Epoxide (S)-3b. GC-FI Chromatograms: (A) Standard of (R,S)-3c. S25
26 References 1. Lin, H.; Chen, Y.; Xu, X.; Xiaa, S. J. Mol. Catal. B: Enzym. 2009, 57, Yang, W.; Xu, J.; Xie, Y.; Xu, Y.; Zhao, G.; Lin, G. Tetrahedron-Asymmetry 2006, 17, Hiratake, J.; Inagaki, M.; Nishioka, T.; Oda, J. Org. Chem. 1998, 53, Traff, A.; Bogar, K.; Warner, M.; Backvall, J. Org. Lett. 2008, 10, Basavaiah,.; Reddy, G.; Chandrashekar, V. Tetrahedron: Asymmetry, 2011, 12, Toda, H.; Imae, R.; Itoh, N. Tetrahedron: Asymmetry, 2012, 23, Basavaiah,.; as, U.; Roy. S. J. Chem. Scien., 2009, 121, Zhang, J.; Wang, J,; Qiu, Z.; Wang, Y. Tetrahedron, 2011, 67, Roman, G.; Vlahaskis, J. Z.; Vukomanovic,.; Nakatsu, K.; Szarek, W. A. ChemMedChem, 2010, 5, S26
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