Supporting Information Synthesis of Natural Cyclopentapeptides ...
Supporting Information Synthesis of Natural Cyclopentapeptides Isolated from Dianthus chinensis
Shengping Zhang, † Zaid Amso, † Luis M. De Leon Rodriguez, ‡ Harveen Kaur, † and Margaret A. Brimble *,†,‡ †
School of Chemical Sciences, The University of Auckland, 23 Symonds Street,
Auckland, 1142, New Zealand
‡
Maurice Wilkins Centre for Molecular Biodiscovery, 3A Symonds Street, The
University of Auckland, Auckland, 1142, New Zealand
1
Table of contents
Figure S1. LC-MS profile of synthetic dianthin I (1)
S3
1
S3
13
Figure S3. C NMR (100 MHz, C5D5N) spectrum of synthetic dianthin I (1)
S4
Figure S4. IR spectrum of synthetic dianthin I (1)
S4
Figure S5. CD spectrum of synthetic dianthin I (1)
S5
Figure S6. LC-MS profile of synthetic pseudostellarin A (2)
S5
Figure S7. 1H NMR (400 MHz, C5D5N) spectrum of synthetic pseudostellarin A (2)
S6
Figure S2. H NMR (400 MHz, C5D5N) spectrum of synthetic dianthin I (1)
13
Figure S8. C NMR (100 MHz, C5D5N) spectrum of synthetic pseudostellarin A (2)
S6
Figure S9. IR spectrum of synthetic pseudostellarin A (2)
S7
Figure S10. CD spectrum of pseudostellarin A(2)
S7
Figure S11. LC-MS profile of synthetic heterophyllin J (3)
S8
1
S8
13
Figure S13. C NMR (100 MHz, C5D5N) spectrum of synthetic heterophyllin J (3)
S9
Figure S14. IR spectrum of synthetic heterophyllin J (3)
S9
Figure S15. CD spectrum of heterophyllin J (3)
S10
Figure S12. H NMR (400 MHz, C5D5N) spectrum of synthetic heterophyllin J (3)
Figure S16. HREIMS characterization of the tetramethyluronium pseudostellarin A derivative (8)
S10
2
dianthin I (1)
Fig.S1. LC-MS profile of synthetic dianthin I (1)
1
Fig.S2. H NMR spectrum (400 MHz, C5D5N) of synthetic dianthin I (1)
3
13
Fig.S3. C NMR (100 MHz, C5D5N) spectrum of synthetic dianthin I (1)
Fig.S4. IR spectrum of synthetic dianthin I (1)
4
25000 20000
θMRE (deg.cm2.dmol-‐1)
15000 10000 5000 0 -5000 -10000 -15000 -20000 -25000 190
210
230
250
270
290
Wavelength (nm)
Fig.S5. CD spectrum of dianthin I (1)
Pseudostellarin A (2)
Fig.S6. LC-MS profile of synthetic pseudostellarin A (2)
5
1
Fig.S7. H NMR spectrum (400 MHz, C5D5N) of synthetic pseudostellarin A λ(2)
13
Fig.S8. C NMR spectrum (100 MHz, C5D5N) of synthetic pseudostellarin A (2)
6
Fig.S9. IR spectrum of synthetic pseudostellarin A (2) 25000
θMRE (deg.cm2.dmol-1)
20000 15000 10000 5000 0 -5000 -10000 -15000 -20000 -25000 190
210
230
250 Wavelength (nm)
270
290
Fig.S10. CD spectrum of pseudostellarin A (2)
7
heterophyllin J (3)
Fig.S11. LC-MS profile of synthetic heterophyllin J (3)
1
Fig.S12. H NMR spectrum (400 MHz, C5D5N) of synthetic heterophyllin J (3)
8
13
Fig.S13. C NMR spectrum (100 MHz, C5D5N) of synthetic heterophyllin J (3)
Fig.S14. IR spectrum of synthetic heterophyllin J (3)
9
35000 30000 25000 θMRE (deg.cm2.dmol-1)
20000 15000 10000 5000 0 -5000 -10000 -15000 -20000 -25000 190
210
230
250 Wavelength (nm)
Fig.S15. CD spectrum of heterophyllin J
270
290
Fig.S16. HREIMS characterization of the tetramethyluronium pseudostellarin A derivative (8)
10
Shengping Zhang, † Zaid Amso, † Luis M. De Leon Rodriguez, ‡ Harveen Kaur, † and Margaret A. Brimble *,†,‡ †
School of Chemical Sciences, The University of Auckland, 23 Symonds Street,
Auckland, 1142, New Zealand
‡
Maurice Wilkins Centre for Molecular Biodiscovery, 3A Symonds Street, The
University of Auckland, Auckland, 1142, New Zealand
1
Table of contents
Figure S1. LC-MS profile of synthetic dianthin I (1)
S3
1
S3
13
Figure S3. C NMR (100 MHz, C5D5N) spectrum of synthetic dianthin I (1)
S4
Figure S4. IR spectrum of synthetic dianthin I (1)
S4
Figure S5. CD spectrum of synthetic dianthin I (1)
S5
Figure S6. LC-MS profile of synthetic pseudostellarin A (2)
S5
Figure S7. 1H NMR (400 MHz, C5D5N) spectrum of synthetic pseudostellarin A (2)
S6
Figure S2. H NMR (400 MHz, C5D5N) spectrum of synthetic dianthin I (1)
13
Figure S8. C NMR (100 MHz, C5D5N) spectrum of synthetic pseudostellarin A (2)
S6
Figure S9. IR spectrum of synthetic pseudostellarin A (2)
S7
Figure S10. CD spectrum of pseudostellarin A(2)
S7
Figure S11. LC-MS profile of synthetic heterophyllin J (3)
S8
1
S8
13
Figure S13. C NMR (100 MHz, C5D5N) spectrum of synthetic heterophyllin J (3)
S9
Figure S14. IR spectrum of synthetic heterophyllin J (3)
S9
Figure S15. CD spectrum of heterophyllin J (3)
S10
Figure S12. H NMR (400 MHz, C5D5N) spectrum of synthetic heterophyllin J (3)
Figure S16. HREIMS characterization of the tetramethyluronium pseudostellarin A derivative (8)
S10
2
dianthin I (1)
Fig.S1. LC-MS profile of synthetic dianthin I (1)
1
Fig.S2. H NMR spectrum (400 MHz, C5D5N) of synthetic dianthin I (1)
3
13
Fig.S3. C NMR (100 MHz, C5D5N) spectrum of synthetic dianthin I (1)
Fig.S4. IR spectrum of synthetic dianthin I (1)
4
25000 20000
θMRE (deg.cm2.dmol-‐1)
15000 10000 5000 0 -5000 -10000 -15000 -20000 -25000 190
210
230
250
270
290
Wavelength (nm)
Fig.S5. CD spectrum of dianthin I (1)
Pseudostellarin A (2)
Fig.S6. LC-MS profile of synthetic pseudostellarin A (2)
5
1
Fig.S7. H NMR spectrum (400 MHz, C5D5N) of synthetic pseudostellarin A λ(2)
13
Fig.S8. C NMR spectrum (100 MHz, C5D5N) of synthetic pseudostellarin A (2)
6
Fig.S9. IR spectrum of synthetic pseudostellarin A (2) 25000
θMRE (deg.cm2.dmol-1)
20000 15000 10000 5000 0 -5000 -10000 -15000 -20000 -25000 190
210
230
250 Wavelength (nm)
270
290
Fig.S10. CD spectrum of pseudostellarin A (2)
7
heterophyllin J (3)
Fig.S11. LC-MS profile of synthetic heterophyllin J (3)
1
Fig.S12. H NMR spectrum (400 MHz, C5D5N) of synthetic heterophyllin J (3)
8
13
Fig.S13. C NMR spectrum (100 MHz, C5D5N) of synthetic heterophyllin J (3)
Fig.S14. IR spectrum of synthetic heterophyllin J (3)
9
35000 30000 25000 θMRE (deg.cm2.dmol-1)
20000 15000 10000 5000 0 -5000 -10000 -15000 -20000 -25000 190
210
230
250 Wavelength (nm)
Fig.S15. CD spectrum of heterophyllin J
270
290
Fig.S16. HREIMS characterization of the tetramethyluronium pseudostellarin A derivative (8)
10
