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1 SUPPLEMENTARY INFRMATIN Wakodecalines A and B, new decaline metabolites isolated from a fungus Pyrenochaetopsis sp. RK10-F058 Toshihiko Nogawa 1, Naoki Kato 2, Takeshi Shimizu 1, Akiko kano 1, Yushi Futamura 1, Shunji Takahashi 2, iroyuki sada 1 1 RIKEN Center for Sustainable Research Science, Chemical biology Research Group, 2-1 irosawa, Wako, Saitama , Japan 2 RIKEN Center for Sustainable Research Science, Natural Product Biosynthesis Research Unit, 2-1 irosawa, Wako, Saitama , Japan Corresponding author Mailing address: RIKEN CSRS, Chemical Biology Research Group, 2-1 irosawa, Wako, Saitama , Japan Phone: (+81) Fax: (+81) [email protected] 1
2 CNTENTS Conformational analysis and computer calculation of ECD spectra of compound 2 / page 3 Figure S1. UV chromatograms of 1 (A) and 2 (B) recorded at 254 nm, and UV and ECD spectra of 1 and 2 (C) / page 17 Figure S2. RESITFMS data of compound 1 / page 18 Figure S3. 1 NMR spectrum of compound 1 / page 19 Figure S4. 13 C NMR spectrum of compound 1 / page 19 Figure S5. SQC spectrum of compound 1 / page 20 Figure S6. 13 C DEPT 135 spectrum of compound 1 / page 20 Figure S7. DQF-CSY spectrum of compound 1 / page 21 Figure S8. MBC spectrum of compound 1 / page 21 Figure S9. phase-sensitive NESY spectrum of compound 1 / page 22 Figure S10. RESITFMS data of compound 2 / page 23 Figure S11. 1 NMR spectrum of compound 2 / page 24 Figure S C NMR spectrum of compound 2 / page 24 Figure S C DEPT 135 spectrum of compound 2 / page 25 Figure S14. SQC spectrum of compound 2 / page 25 Figure S15. DQF-CSY spectrum of compound 2 / page 26 Figure S16. MBC spectrum of compound 2 / page 26 Figure S17. Key 2D NMR correlations of compound 2 / page 27 Figure S18. phase-sensitive NESY spectrum of compound 2 / page 27 Figure S19. UV and mass chromatograms of L-FDLA derivatives derived from 1 (A), D-N-methylated-serine (B), and L-N-methyl-serine (C) Figure S20. ECD spectra of 7s prepared from 1 and 2 / page 28 Scheme S1. Plausible biosynthetic pathway for wakodecaline A (1) / page 28 2
3 Conformational analysis and computer calculation of ECD spectra of compound 2 Conformational analysis using Spartan '16 Conformer Distribution with Molecular Mechanics/MMFF ptimization using Spartan '16 Equilibrium Geometry with artree-fock/st-3g DFT calculation using Gaussian 09* ptimization at B3LYP/6-31G (d) level #p opt b3lyp/6-31g(d) geom=connectivity TDDFT calculation using Gaussian 09* Frequency analysis at ωb97xd/6-31g (d) level #p td=(nstate=6) wb97xd/6-31g(d)/auto geom=connectivity *Gaussian 09, Revision E.01, M. J. Frisch, G. W. Trucks,. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson,. Nakatsuji, M. Caricato, X. Li,. P. ratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. ada, M. Ehara, K. Toyota, R. Fukuda, J. asegawa, M. Ishida, T. Nakajima, Y. onda,. Kitao,. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. gliaro, M. Bearpark, J. J. eyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann,. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. chterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels,. Farkas, J. B. Foresman, J. V. rtiz, J. Cioslowski, and D. J. Fox, Gaussian, Inc., Wallingford CT, Starting geometry for conformational analysis C C C C C C
4 C C C C C C C C C C N C C C C C C C C C
5 Conformer 1 (the lowest energy conformer) Energy = a.u. Symbol X Y Z C C C C C
6 C C C C C C C C C C C N C C C C C C C C C
7 Conformer 2 Energy = a.u. Symbol X Y Z C C C C
8 C C C C C C C C C C C C N C C C C C C C C C
9 Conformer 3 Energy = a.u. Symbol X Y Z C C C
10 C C C C C C C C C C C C C N C C C C C C C C C
11 Conformer 4 Energy = a.u. Symbol X Y Z C C
12 C C C C C C C C C C C C C C N C C C C C C C C C
13 Conformer 5 Energy = a.u. Symbol X Y Z C
14 C C C C C C C C C C C C C C C N C C C C C C C C C
15
16 conformer 1 (38.6%) conformer 2 (23.4%) conformer 3 (15.3%) conformer 4 (13.5%) conformer 5 (1.2%) Structures and populations of the low-energy conformers ( 1%) of 2 16
17 A Auto-ScaledChromatogram AU nm Minutes Minutes B 0.80 Auto-ScaledChromatogram AU Minutes C UV spectrum of 1 UV spectrum of nm ECD spectrum of nm ECD spectrum of nm nm Figure S1. UV chromatograms of 1 (A) and 2 (B) recorded at 254 nm, and UV and ECD spectra of 1 and 2 (C) 17
18 F032 50dil with C3 Sy_ _G058_N02_01 (0.467) Is (0,0.05) C2536N6 1: TF MS ES e m/z Sy_ _G058_N02_01 23 (0.467) AM (Cen,1, 50.00, Ar, ,0.00,0.00) 1: TF MS ES e3 100 % % m/z Monoisotopic Mass, Even Electron Ions 1052 formula(e) evaluated with 3 results within limits (up to 50 closest results for each mass) Elements Used: C: : N: 0-15 : 0-15 F032 50dil with C3 Sy_ _G058_N02_01 23 (0.467) AM (Cen,1, 50.00, Ar, ,0.00,0.00) 1: TF MS ES- 100 % e m/z Minimum: -1.5 Maximum: Mass Calc. Mass mda PPM DBE i-fit Norm Conf(%) Formula C25 36 N C10 32 N C26 32 N5 2 Figure S2. RESITFMS data of compound 1 18
19 N residual CCl X : parts per Million : Proton Figure S3. 1 NMR spectrum of compound X : parts per Million : Carbon13 Figure S4. 13 C NMR spectrum of compound 1 19
20 Y : parts per Million : Carbon X : parts per Million : Proton Figure S5. SQC spectrum of compound (thousandths) X : parts per Million : Carbon13 Figure S6. 13 C DEPT 135 spectrum of compound 1 20
21 Y : parts per Million : Proton X : parts per Million : Proton Y : parts per Million : Carbon Figure S7. DQF-CSY spectrum of compound X : parts per Million : Proton Figure S8. MBC spectrum of compound
22 Y : parts per Million : Proton X : parts per Million : Proton Figure S9. phase-sensitive NESY spectrum of compound 1 22
23 F028 50dil with C3 Sy_ _G058_N01_02 (0.260) Is (0,0.05) C2534N6 1: TF MS ES e m/z Sy_ _G058_N01_02 12 (0.260) AM (Cen,1, 50.00, Ar, ,0.00,0.00) 1: TF MS ES e4 100 % % m/z Monoisotopic Mass, Even Electron Ions 1047 formula(e) evaluated with 3 results within limits (up to 50 closest results for each mass) Elements Used: C: : N: 0-15 : 0-15 F028 50dil with C3 S y _ _ G _ N 0 1 _ ( ) A M ( C e n, 1, , Ar, ,0.00,0.00)1 : T F M S E S e % Minimum: -1.5 Maximum: Mass Calc. Mass mda PPM DBE i-fit Norm Conf(%) Formula C10 30 N C25 34 N C26 30 N5 2 Figure S10. RESITFMS data of compound m/z 23
24 N X : parts per Million : Proton Figure S11. 1 NMR spectrum of compound 2 (thousandths) X : parts per Million : Carbon13 Figure S12 13 C NMR spectrum of compound 2 24
25 (thousandths) X : parts per Million : Carbon13 Figure S C DEPT 135 spectrum of compound 2 Y : parts per Million : Carbon X : parts per Million : Proton Figure S14. SQC spectrum of compound (thousandths) 25
26 Y : parts per Million : Proton X : parts per Million : Proton Y : parts per Million : Carbon Figure S15. DQF-CSY spectrum of compound X : parts per Million : Proton Figure S16. MBC spectrum of compound (thousandths) 60.0
27 A N 25 1 B DQF-CSY MBC NESY Figure S17. Key 2D NMR correlations of compound 2 Y : parts per Million : Proton A: MBC correlations, B: NESY correlations X : parts per Million : Proton Figure S18. phase-sensitive NESY spectrum of compound 2 27
28 A N-methyl-serine L-FDLA derivative derived from compound min UV chromatogram at 254 nm m/z: 414 [M+] + Mass chromatogram by m/z 414 B D-N-methylated-serine L-FDLA derivative min UV chromatogram at 254 nm m/z: 414 [M+] + Mass chromatogram by m/z 414 C L-N-methylated-serine L-FDLA derivative min UV chromatogram at 254 nm m/z: 414 [M+] + Mass chromatogram by m/z retention time (min) m/z Figure S19. UV and mass chromatograms of L-FDLA derivatives derived from 1 (A), D-N-methylated-serine (B), and L-N-methyl-serine (C) 10 7 from from N phomasetin (3) Figure S20. ECD spectra of 7s prepared from 1 and 2 [] N + Scheme S1. Plausible biosynthetic pathway for wakodecaline A (1) N spiro-intermediate + 2 N wakodecaline A (1) 28
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