Synthesis and Evaluation of Antibacterial Activity of Bottromycins
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1 Supporting Information Synthesis and Evaluation of Antibacterial Activity of Bottromycins Takeshi Yamada,,, Miu Yagita, Yutaka Kobayashi, Goh Sennari, Hiroyuki Shimamura, Hidehito Matsui, Yuki Horimatsu, Hideaki Hanaki, Tomoyasu Hirose,, Satoshi Ōmura*, and Toshiaki Sunazuka*,, Kitasato Institute for Life Sciences, Kitasato University Graduate School of Infection Control Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo , Japan S-1
2 Table of Content Comparison of 1 H and 13 C NMR data of synthetic bottromycin B 2 (2) with naturally occurring 2 S-3 Spectra data of 19 S-3 1 H and 13 C NMR charts of 19 S-5 1 H and 13 C NMR charts of 27 S-7 1 H and 13 C NMR charts of 28 S-9 1 H and 13 C NMR charts of 29 S-11 1 H and 13 C NMR charts of Bottromycin B 2 (2) S-13 1 H and 13 C NMR charts of 30 S-15 1 H and 13 C NMR charts of 34 S-17 1 H and 13 C NMR charts of 36 S-19 1 H and 13 C NMR charts of 38 S-21 1 H and 13 C NMR charts of 40 S-23 1 H and 13 C NMR charts of 43 S-25 1 H and 13 C NMR charts of 46 S-27 1 H and 13 C NMR charts of C-33-demethyl-bottromycin A 2 (25) S-29 1 H and 13 C NMR charts of 41 S-31 1 H and 13 C NMR charts of 44 S-33 1 H and 13 C NMR charts of 47 S-35 1 H and 13 C NMR charts of C-33-demethyl-bottromycin B 2 (26) S-37 1 H and 13 C NMR charts of 31 S-39 1 H and 13 C NMR charts of 35 S-41 1 H and 13 C NMR charts of 37 S-43 1 H and 13 C NMR charts of 39 S-45 1 H and 13 C NMR charts of 42 S-47 1 H and 13 C NMR charts of 45 S-49 1 H and 13 C NMR charts of 48 S-51 1 H and 13 C NMR charts of 49 S-53 1 H and 13 C NMR charts of 50 S-55 1 H, 13 C, 1 H- 1 H COSY, HMQC, HMBC NMR charts of 51 S-57 1 H, 13 C, 1 H- 1 H COSY NMR charts of 55 S-62 1 H, 13 C, 1 H- 1 H COSY NMR charts of 56 S-65 1 H, 13 C, 1 H- 1 H COSY NMR charts of 57 S-68 1 H, 13 C, 1 H- 1 H COSY, ROESY NMR charts of 58 S-71 S-2
3 NMR data of naturally occurring bottromycin B 2 and synthetic bottromycin B 2 7 O HN N 3 O H 1 NH 25 O H N 31 N N H H N O 34 H O O S OMe N 45 Position Naturally occurring Bottromycin B 2 Synthetic Bottromycin B 2 Amino acid δ C δ H (J in Hz) δ C δ H (J in Hz) residue N (t-like) 4.05 (t-like) (dd, J = 12.2, 2.7 Hz) (complex m) 3.77 (dd, J = 12.2, 4.1 Hz) 3.83 (dd, J = 12.2, 4.1 Hz) Glycine N (m) (complex m) (m) (complex m) (m) 2.28 (m) (complex m) 2.31 (m) L-Proline (dd, J = 9.3, 2.1 Hz) (dd, J = 9.5, 2.1 Hz) N (m) (m) (m) (m) (m) (d, J = 6.6 Hz) (d, J = 6.5 Hz) L-Valine (d, J = 6.4 Hz) (d, J = 6.5 Hz) N (d, J = 10.5 Hz) 7.10 (d, J = 10.5 Hz) (d, J = 10.8 Hz) (d, J = 10.8 Hz) (brs) (s) t-leucine (brs) (s) (brs) (s) N (s) (s) t-leucine S-3
4 (brs) (s) (brs) (s) (brs) (s) N (d, J = 8.8 Hz) 6.92 (d, J = 8.1 Hz) (dd, J = 8.6, 4.1 Hz) (dd, J = 8.1, 4.2 Hz) (m) (m) (d, J = 7.1 Hz) (d, J = 7.1 Hz) (brd) (d, J = 7.5 Hz) (brt) (t, J = 7.5 Hz) (m) (brt) (t, J = 7.5 Hz) (brd) (d, J = 7.5 Hz) N (d, J = 6.4 Hz) 7.47 (d, J = 6.0 Hz) (ddd, J = 7.4, 6.8, (m) Hz) N (d, J = 3.3 Hz) (d, J = 3.3 Hz) (d, J = 3.3 Hz) (d, J = 3.3 Hz) S (dd, J = 16.8, 5.5 Hz) (dd, J = 16.9, 5.5 Hz) 3.06 (dd, J = 16.8, 6.8 Hz) 3.01 (dd, J = 16.9, 6.5 Hz) (s) (s) MePhe Thia-β-Ala N-Phthaloyl-L-tert-leucine 2-tert-butyldiphenylsilyloxyethylamide 19 colorless oil; 1 H NMR (500 MHz, CD 3 OD) δ 8.08 (brdd, J = 5.0, 5.0 Hz, 1H), 7.86 (m, 2H), 7.82 (m, 2H), (4H), (6H), 4.87 (s, 1H), 3.68 (m, 2H), 3.38 (m, 1H), 3.34 (m, 1H), 1.14 (s, 9H), 0.95 (s, 9H); 13 C NMR (125 MHz, CD 3 OD) δ 170.2, 170.1, 170.0, (4C), (2C), (2C), (2C), 130.9, 130.8, (4C), (2C), 63.6, 63.5, 42.9, 37.2, 28.7 (3C), 27.2 (3C), 19.9; IR (Diamond prism) 3346, 2958, 2858, 2364, 1773, 1708, 1667, 1539, 1469, 1428, 1370, 1328, 1104, 1086, 900, 822, 701, 613, 503 cm -1 ; HRMS (ESI-TOF) m/z [M+Na] + calcd for [C 32 H 38 N 2 Na 1 O 4 Si 1 ] , found ; [α] 21 D (c 1.0, CHCl 3 ). S-4
5 1 H NMR (500 MHz) spectra of 19 in CD 3 OD S-5
6 13 C NMR (125 MHz) spectra of 19 in CD 3 OD S-6
7 1 H NMR (500 MHz) spectra of 27 in CDCl 3 S-7
8 13 C NMR (125 MHz) spectra of 27 in CDCl 3 S-8
9 1 H NMR (500 MHz) spectra of 28 in CDCl 3 S-9
10 13 C NMR (125 MHz) spectra of 28 in CDCl 3 S-10
11 1 H NMR (500 MHz) spectra of 29 in CD 3 OD S-11
12 13 C NMR (125 MHz) spectra of 29 in CD 3 OD S-12
13 1 H NMR (500 MHz) spectra of Bottromycin B 2 (2) in CDCl 3 S-13
14 13 C NMR (125 MHz) spectra of Bottromycin B 2 (2) in CDCl 3 S-14
15 1 H NMR (500 MHz) spectra of 30 in CDCl 3 S-15
16 13 C NMR (125 MHz) spectra of 30 in CDCl 3 S-16
17 1 H NMR (500 MHz) spectra of 34 in CDCl 3 S-17
18 13 C NMR (125 MHz) spectra of 34 in CDCl 3 S-18
19 1 H NMR (500 MHz) spectra of 36 in CDCl 3 S-19
20 13 C NMR (125 MHz) spectra of 36 in CDCl 3 S-20
21 1 H NMR (500 MHz) spectra of 38 in CDCl 3 S-21
22 13 C NMR (125 MHz) spectra of 38 in CDCl 3 S-22
23 1 H NMR (500 MHz) spectra of 40 in CDCl 3 S-23
24 13 C NMR (125 MHz) spectra of 40 in CDCl 3 S-24
25 1 H NMR (500 MHz) spectra of 43 in CDCl 3 S-25
26 113 C NMR (125 MHz) spectra of 43 in CDCl 3 S-26
27 1 H NMR (500 MHz) spectra of 46 in CD 3 OD S-27
28 13 C NMR (125 MHz) spectra of 46 in CDCl 3 S-28
29 1 H NMR (500 MHz) spectra of C-33-demethyl-bottromycin A 2 (25) in CDCl 3 S-29
30 13 C NMR (125 MHz) spectra of C-33-demethyl-bottromycin A 2 (25) in CDCl 3 S-30
31 1 H NMR (500 MHz) spectra of 41 in CDCl 3 S-31
32 13 C NMR (125 MHz) spectra of 41 in CDCl 3 S-32
33 1 H NMR (500 MHz) spectra of 44 in CDCl 3 S-33
34 13 C NMR (125 MHz) spectra of 44 in CDCl 3 S-34
35 1 H NMR (500 MHz) spectra of 47 in CDCl 3 S-35
36 13 C NMR (125 MHz) spectra of 47 in CDCl 3 S-36
37 1 H NMR (500 MHz) spectra of C-33-demethyl-bottromycin B 2 (26) in CDCl 3 S-37
38 13 C NMR (125 MHz) spectra of C-33-demethyl-bottromycin B 2 (26) in CDCl 3 S-38
39 1 H NMR (500 MHz) spectra of 31 in CDCl 3 S-39
40 13 C NMR (125 MHz) spectra of 31 in CDCl 3 S-40
41 1 H NMR (500 MHz) spectra of 35 in CDCl 3 S-41
42 13 C NMR (125 MHz) spectra of 35 in CDCl 3 S-42
43 1 H NMR (500 MHz) spectra of 37 in CDCl 3 S-43
44 13 C NMR (125 MHz) spectra of 37 in CDCl 3 S-44
45 1 H NMR (500 MHz) spectra of 39 in CDCl 3 S-45
46 13 C NMR (125 MHz) spectra of 39 in CDCl 3 S-46
47 1 H NMR (500 MHz) spectra of 42 in CDCl 3 S-47
48 13 C NMR (125 MHz) spectra of 42 in CDCl 3 S-48
49 1 H NMR (500 MHz) spectra of 45 in CDCl 3 S-49
50 13 C NMR (125 MHz) spectra of 45 in CDCl 3 S-50
51 1 H NMR (500 MHz) spectra of 48 in CDCl 3 S-51
52 13 C NMR (125 MHz) spectra of 48 in CDCl 3 S-52
53 1 H NMR (500 MHz) spectra of 49 in CDCl 3 S-53
54 13 C NMR (125 MHz) spectra of 49 in CDCl 3 S-54
55 1 H NMR (500 MHz) spectra of 50 in CDCl 3 S-55
56 13 C NMR (125 MHz) spectra of 50 in CDCl 3 S-56
57 1 H NMR (500 MHz) spectra of 51 in CDCl 3 S-57
58 13 C NMR (125 MHz) spectra of 51 in CDCl 3 S-58
59 1 H- 1 H COSY spectra of 51 in CDCl 3 S-59
60 HMQC spectra of 51 in CDCl 3 S-60
61 HMBC spectra of 51 in CDCl 3 S-61
62 1 H NMR (500 MHz) spectra of 55 in CDCl 3 S-62
63 13 C NMR (125 MHz) spectra of 55 in CDCl 3 S-63
64 1 H - 1 H COSY spectra of 55 in CDCl 3 S-64
65 1 H NMR (500 MHz) spectra of 56 in CDCl 3 S-65
66 13 C NMR (125 MHz) spectra of 56 in CDCl 3 S-66
67 1 H - 1 H COSY spectra of 56 in CDCl 3 S-67
68 1 H NMR (500 MHz) spectra of 57 in CDCl 3 S-68
69 13 C NMR (125 MHz) spectra of 57 in CDCl 3 S-69
70 1 H - 1 H COSY spectra of 57 in CDCl 3 S-70
71 1 H NMR (500 MHz) spectra of 58 in CDCl 3 S-71
72 13 C NMR (125 MHz) spectra of 58 in CDCl 3 S-72
73 1 H - 1 H COSY spectra of 58 in CDCl 3 S-73
74 ROESY spectra of 58 in CDCl 3 S-74
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