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1 SUPPORTING INFORMATION Heronamides A C, new polyketide macrolactams from an Australian marine-derived Streptomyces sp. A biosynthetic case for synchronized tandem electrocyclization. Ritesh Raju, Andrew M. Piggott, Melissa M. Conte and Robert J. Capon* Institute for Molecular Bioscience, The University of Queensland, St Lucia, Queensland, 4072, Australia Table of Contents Figure S1a. 1 H NMR (600 MHz, methanol-d 4 ) and UV-vis (inset) spectra of heronamide A (1)...2 Figure S1b. COSY spectrum (600 MHz, methanol-d 4 ) of heronamide A (1)...3 Figure S1c. HSQC spectrum (600 MHz, methanol-d 4 ) of heronamide A (1)...4 Figure S1d. HMBC spectrum (600 MHz, methanol-d 4 ) of heronamide A (1)...5 Figure S1e. ROESY spectrum (600 MHz, methanol-d 4 ) of heronamide A (1)...6 Figure S1f. IR spectrum for heronamide A (1)...7 Figure S2a. 1 H NMR (600 MHz, methanol-d 4 ) and UV-vis (inset) spectra of heronamide B (2)...8 Figure S2b. COSY spectrum (600 MHz, methanol-d 4 ) of heronamide B (2)...9 Figure S2c. HSQC spectrum (600 MHz, methanol-d 4 ) of heronamide B (2)...10 Figure S2d. HMBC spectrum (600 MHz, methanol-d 4 ) of heronamide B (2)...11 Figure S2e. ROESY spectrum (600 MHz, methanol-d 4 ) of heronamide B (2)...12 Figure S2f. 1 H NMR (600 MHz, CDCl 3 ) spectrum of 13-methylmyristic acid...13 Figure S3a. 1 H NMR (600 MHz, pyridine-d 5 ) and UV-vis (inset) spectra of heronamide C (3)...14 Figure S3b. COSY spectrum (600 MHz, methanol-d 4 ) of heronamide C (3)...15 Figure S3c. HSQC spectrum (600 MHz, methanol-d 4 ) of heronamide C (3)...16 Figure S3d. HMBC spectrum (600 MHz, methanol-d 4 ) of heronamide C (3)...17 Figure S3e. ROESY spectrum (600 MHz, methanol-d 4 ) of heronamide C (3)...18 Figure S4. 1 H NMR (600 MHz, methanol-d 4 ) and UV-vis (inset) spectra of heronamide A acetonide (1a)...19 Figure S5a. 1 H NMR (600 MHz, methanol-d 4 ) and UV-vis (inset) spectra of heronamide A triacetate (1b)...20 Figure S5b. 1 H NMR (600 MHz, CDCl 3 ) and UV-vis (inset) spectra of heronamide A triacetate (1b)...21 Figure S6. 1 H NMR (600 MHz, methanol-d 4 ) and UV-vis (inset) spectra of heronamide C diacetate (3a)...22 Figure S7a. 1 H NMR (600 MHz, CDCl 3 ) spectra of R and S Mosher ester of heronamide A acetonide...23 Figure S7b. LC-MS trace analysis for Mosher esters for heronamide A acetonide...24 Figure S8. Reported Streptomyces polyketide 20-membered macrolactams...25 Figure S9. Other reported polyketide macrolactams...26 Table S1. NMR (600 MHz, methanol-d 4 ) data for heronamide A (1)...27 Table S2. NMR (600 MHz, methanol-d 4 ) data for heronamide B (2)...28 Table S3. NMR (600 MHz, pyridine-d 5 ) data for heronamide C (3)...29 Table S4. NMR (600 MHz, methanol-d 4 ) data for heronamide A acetonide (1a)...30 Table S5a. NMR (600 MHz, methanol-d 4 ) data for heronamide A triacetate (1b)...31 Table S5b. NMR (600 MHz, CDCl 3 ) data for heronamide A triacetate (1b)...32 Table S6. NMR (600 MHz, methanol-d 4 ) data for heronamide C diacetate (3a)...33 Table S7. Δδ (=δ S -δ R ) data for the S- and R-MTPA-heronamide A acetonide Mosher esters
2 Figure S1a. 1 H NMR (600 MHz, methanol-d 4 ) and UV-vis (inset) spectrum of heronamide A (1) 2
3 Figure S1b. COSY spectrum (600 MHz, methanol-d 4 ) of heronamide A (1) 3
4 Figure S1c. HSQC spectrum (600 MHz, methanol-d 4 ) of heronamide A (1) 4
5 Figure S1d. HMBC spectrum (600 MHz, methanol-d 4 ) of heronamide A (1) 5
6 Figure S1e. ROESY spectrum (600 MHz, methanol-d 4 ) of heronamide A (1) 6
7 Figure S1f. IR spectrum of heronamide A (1) 7
8 Figure S2a. 1 H NMR (600 MHz, methanol-d 4 ) and UV-vis (inset) spectrum of heronamide B (2) 8
9 Figure S2b. COSY spectrum (600 MHz, methanol-d 4 ) of heronamide B (2) 9
10 Figure S2c. HSQC spectrum (600 MHz, methanol-d 4 ) of heronamide B (2) 10
11 Figure S2d. HMBC spectrum (600 MHz, methanol-d 4 ) of heronamide B (2) 11
12 Figure S2e. ROESY spectrum (600 MHz, methanol-d 4 ) of heronamide B (2) 12
13 Figure S2f. 1 H NMR (600 MHz, CDCl 3 ) spectrum of 13-methylmyristic acid for comparison with isomyristic acid signals in NMR spectra of 2 13
14 Figure S3a. 1 H NMR (600 MHz, pyridine-d 5 ) and UV-vis (inset) spectrum of heronamide C (3) 14
15 Figure S3b. COSY spectrum (600 MHz, methanol-d 4 ) of heronamide C (3) 15
16 Figure S3c. HSQC spectrum (600 MHz, methanol-d 4 ) of heronamide C (3) 16
17 Figure S3d. HMBC spectrum (600 MHz, methanol-d 4 ) of heronamide C (3) 17
18 Figure S3e. ROESY spectrum (600 MHz, methanol-d 4 ) of heronamide C (3) 18
19 Figure S4. 1 H NMR (600 MHz, methanol-d 4 ) and UV-vis (inset) spectrum of heronamide A acetonide (1a) 19
20 Figure S5a. 1 H NMR (600 MHz, methanol-d 4 ) and UV-vis (inset) spectrum of heronamide A triacetate (1b) 20
21 Figure S5b. 1 H NMR (600 MHz, CDCl 3 ) spectrum of heronamide A triacetate (1b) 21
22 Figure S6. 1 H NMR (600 MHz, methanol-d 4 ) and UV-vis (inset) spectrum of heronamide C diacetate (3a) 22
23 Figure S7a. 1 H NMR (600 MHz, CDCl 3 ) spectra of R and S Mosher esters of heronamide A acetonide (1a) 23
24 Figure S7b. HPLC trace analysis (210 nm) for A) heronamide A acetonide (1a), B) S- MTPA ester of heronamide A acetonide (1c), C) R-MTPA ester of heronamide A acetonide (1d). HPLC-DAD-ESI(±) MS conditions (Zorbax C 8 column, mm, 5 µm, 1 ml/min, gradient from % MeCN/H 2 O (isocratic 0.05% formic acid) over 15 min, with a hold at 100 % MeCN for 5 min. 24
25 HO HO OH N O HO NH O HO OH O NH HO O NH BE cyclomenol BE (cf GT32-A) GT32-B MeHN O O H N HO O O H N OH O OH O HO NH OH O vicenistatin vicenistatin M ML-449 Figure S8. Reported Streptomyces polyketide 20-membered macrolactams 25
26 HO NH HO OH OH HN HO OH O OH O aureoverticillactam salinilactam Figure S9. Other reported polyketide macrolactams 26
27 Table S1. NMR (600 MHz, methanol-d 4 ) data for heronamide A (1) pos δ H, mult (J in Hz) δ C COSY ROESY 1 H- 13 C HMBC , ddd (9.2, 7.2, 2.4) , , 3, 4, 15, , dd (10.8, 7.2) , 4 1, 2, , ddd (10.8, 9.8, 2.4) , , d (9.8) , 7, 13 3, 7, , m a , 12 5, 13 8, 9, , dd (11.4, 4.2) , 9 12, 28 7, 9, , dd (4.8, 4.2) , 10 7, 8, 10, , m b , , , m b , , 9, , m , 11, 13 8, 29 7, 13, , d (10.8) , 7, 11, 15 15, , dd (9.2, 8.6) , , 3, 4, 14, 16, 17, , m c , , m c α, 18β 15 18α 2.50, m d , 18β, 19 16, 17 18β 1.81, ddd (13.1, 7.8, 7.8) 17, 18α, 19 17, 19, , m c a/b, 20a/b 20a 2.46, m d , 20b, 21 19, 21, 22 20b 2.43, m d 19, 20a, 21 18, 19, 21, , dt (14.8, 7.5) a/b, 22 20, , dd (14.8, 10.4) , 23 20, , dd (14.5, 10.4) , , dt (14.5, 7.2) , 25 22, , m a , , 26, , sxt (7.4) , 27 25, , t (7.4) , , s , 8 5, 6, , s , 14, 15 [ a-d ] overlapping signals 27
28 Table S2. NMR (600 MHz, methanol-d 4 ) data for heronamide B (2) pos δ H, mult (J in Hz) δ C COSY ROESY 1 H- 13 C HMBC , dd (10.5, 10.1) , 17 4, 16 1, 3, 4, , dd (15.1, 10.1) , , dd (15.1, 11.0) , 5 2, , m a , 7, , m b , , 12, , dd (11.6, 4.2) , 9 12, , m , , m c , 11 9, , m c , 12 7, 9, , dd (10.5, 9.7) , 11, 13 8, 28, 29 7, 13, * , , d (16.0) , 14, 17, , dd (16.0, 9.7) , 17 2, 18α, 29 14, , m , 16, 18α, 18β 3, 15, 19 2, 15, 16 18α 2.15, ddd (13.3, 4.8, 2.6) , 18β, 19 16, 19 16, 17 18β 1.60, m 17, 18α, 19 17, 19, , m α, 18β, 20 17, , m b , , 19, , dt (15.0, 7.4) , , , dd (15.0, 10.4) , , 23, , dd (15.0, 10.4) , , , m a , 25 22, , m , , 24, 26, , m , 27 24, 25, , t (7.4) , , s , 8, 12 5, 6, , s , 16 13, 14, 15 [ a-c ] overlapping signals, * obscured by H 2 O signal 28
29 Table S3. NMR (600 MHz, pyridine-d 5 ) data for heronamide C (3) pos δ H, mult (J in Hz) δ C COSY ROESY 1 H- 13 C HMBC , m a , dd (14.9, 11.0) , , m b , , m a , 7, , br d (8.2) , , dd (8.2, 3.0) , , 7, , dd, (8.9, 3.0) , , m b , , m a , , m b , , m b , d (11.4) , 14, 17, , dd (14.9, 11.4) , 17 18β, , ddd (14.9, 10.5, 5.4) , 18α, 18β 15, α 2.53, m , 18β, , 17 18β 2.07, dd (23.1, 10.5) 17, 18α, , , m α, 18β, 20a/b 17, 21 20a 2.45, ddd (14.3, 7.3, 7.1) , 20b, , 19, 21, 22 20b 2.39, ddd (14.3, 7.1, 6.7) 19, 20a, 21 18, 19, 21, , dt (15.1, 7.1) a/b, , , m b , , dd (14.8, 10.3) , 24 21, 24, , dt, (14.8, 6.9) , 25 22, 25, , td (7.5, 6.9) , 26 23, 24, 26, , sxt, (7.5) , 27 24, 25, , t (7.5) , , s , 9 5, 6, , s , 14, 15 NH 7.98, d (10.3) [ a,b ] overlapping signals 29
30 Table S4. NMR (600 MHz, methanol-d 4 ) data for heronamide A acetonide (1a) pos δ H, mult (J in Hz) δ C COSY ROESY 1 H- 13 C HMBC , ddd (9.2, 7.1, 2.3) , , 3, 4, 15, , m a , 4 1, , ddd (12.0, 10.2, 2.1) , , m a , 7, , m b , , 12, , dd (11.1, 6.0) , 9 12, 28, 31 9, , dd (6.0, 3.8) , 10 12, 31 7, 8, 10, , ddd (9.8, 3.8, 2.8) , 11 8, , m c , 12 7, 9, 12, , br dd (10.9, 8.4) , 11, 13 8, 9 7, 10, 11, 13, , d (10.9) , 15 11,15, , dd (9.4, 8.6) , 16 2, 13 2, 3, 13, 14, 16, 17, , m d , 17 14, , m d , 18α, 18β 18α 2.50, m , 18β, 19 16, 17 18β 1.82, m b 17, 18α, , m d α, 18β, 20a/b 20a 2.47, m e , 20b, 21 18, 19, 21, 22 20b 2.43, m e 19, 20a, 21 18, 19, 21, , dt (14.7, 7.5) a/b, 22 20, , dd (14.7, 10.4) , 23 20, , m c , , , dt (14.5, 7.0) , 25 22, 25, , m , , 24, 26, , sxt (7.4) , 27 25, , t (7.4) , , s , 8 6, , s , 16 13, 14, , s , , s , 9 30, [ a-d overlapping signals] 30
31 Table S5a. NMR (600 MHz, methanol-d 4 ) data for heronamide A triacetate (1b) pos δ H, mult (J in Hz) δ C COSY ROESY 1 H- 13 C HMBC , ddd (9.5, 7.2, 1.8) , , 3, 4, 15, , dd (10.6, 7.2) , 4 1, 2, , ddd (10.6, 10.0, 1.8) , , , d a (10.0) , 7 3, 7, , m , 12 5, 13 5, 8, 12, , dd (12.3, 3.9) , 9 12, 28 7, 9, , m b , , ddd (8.9, 5.4, 2.4) , , 9, , m c , 12 7, 9, , dd (10.4, 10.3) , 11, 13 8, 28, 29 6, 7, 10, 13, , d (10.9) , 15 15, * , , 3, 13, 14, 16, 17, , dd (9.7, 5.7) , 17 18β, * , 18α, 18β 18α 15 18α 2.62, ddd (13.8, 7.7, 7.2) , 18β, 19 17, 19 16, 17, 19, 20 18β 1.89, ddd (13.8, 11.4, 5.8) 17, 18α, 19 17, 19, , dddd (7.2, 6.9, 6.4, 5.8) α, 18β, 20a/b 18α, 20a 21 20a 2.45, m , 20b, , 19, 21, 22 20b 2.41, m 19, 20a, 21 18, 19, 21, , dt a (14.8, 7.4) a/b, 22 20, , m c , , dd (14.9, 10.4) , 24 21, , dt b (14.9, 7.2) , 25 22, , m d , 26 23, 24, 26, , sxt (7.4) , 27 24, 25, , t (7.4) , , s , 8, 12 5, , s , 16 13, 14, 15 8-OC(O)Me 2.07, s d OC(O) 9-OC(O)Me 1.98, s OC(O) 17-OC(O)Me 2.03, s OC(O) 8-OC(O) OC(O) OC(O) [ a,b ] partially overlapping signals, [ c,d ] overlapping signals, * obscured by solvent signal 31
32 Table S5b. NMR (600 MHz, CDCl 3 ) data for heronamide A triacetate (1b) pos δ H, mult (J in Hz) δ C COSY ROESY 1 H- 13 C HMBC , ddd (8.9, 7.5, 2.2) , 15 5, 15 1, 3, 4, 15, , m a , 4 2, , dd (10.4, 9.7) , , d (9.7) , 7 3, 7, , dd (12.4, 9.8) , 12 5, 13 5, 8, 12, , dd (12.4, 4.0) , 9 12, , m b , , ddd (8.2, 5.5, 2.6) , 11 8, 9, , m c , 12 12, 13 7, 9, , dd, (11.0, 9.8) , 11, 13 8, 11, 29 7, 11, , d (11.0) , 15 15, , dd (9.6, 8.9) , 16 2, 13, 17, 19 2, 3, 13, 14, 16, 17, , dd (9.6, 5.6) , , ddd (13.9, 11.6, 5.6) , 18α, 18β 15, 18α, α 2.53, m d , 18β, , 20 18β 1.82, ddd (13.9, 12.0, 6.0) 17, 18α, 19 17, 19, , m α, 18β, 20a/b 15, 17, 18α, 20b 17 20a 2.50, m d , 20b, 21 21, 22 20b 2.35, ddd (15.0, 13.9, 7.9) 19, 20a, 21 19, 22 18, 19, 21, , ddd a (14.8, 7.9, 7.2) a/b, 22 20, , m c , 23 20b , dd (14.9, 10.6) , , m b , 25 22, 25, , m , , 26, , sxt (7.3) , 27 24, 25, , t (7.3) , , s , 8 5, 6, , s , 16 13, 14, 15 8-OC(O)Me 2.09, s OC(O) 9-OC(O)Me 2.02, s OC(O) 17-OC(O)Me 2.01, s OC(O) 8-OC(O) OC(O) OC(O) [ a-d ] overlapping signals 32
33 Table S6. NMR (600 MHz, methanol-d 4 ) data for heronamide C diacetate (3a) pos δ H, mult (J in Hz) δ C COSY 1 H- 13 C HMBC , d (15.1) , dd (15.1, 10.5) , 4 1, , dd (15.1, 10.5) , , d a (15.1) , 4, , br d (8.2) , , dd (9.3, 2.6) , 9 10, 8-OC(O) , m b , , dd (10.8, 9.3) , , dd (11.0, 10.8) , 12 8, , dd c (15.1, 11.1) , , d a (15.1) , d (11.0) , 17, , m a , , m d , 18α, 18β 18α 2.45, m , 18β, 19 18β 1.85, m 17, 18α, , m α,18β, , m , , m d , , m b , , m c , , m d , , m , 26 26, , sxt, (7.3) , 27 24, 25, , t (7.3) , , s , 6, , s , 14, 15 8-OC(O)Me 2.09, s OC(O) 9-OC(O)Me 2.03, s OC(O) 8-OC(O) OC(O) [ a,c partially overlapping signals] [ b, d overlapping signals] 33
34 Table S7. Δδ SR (= δ S δ R ) data for the S- and R-MTPA-heronamide A acetonide Mosher esters Proton Chemical shift (δ) Free alcohol (1a) S-MTPA (1c) R-MTPA (1d) Δδ SR (Hz)
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