Marine natural occurring 2,5-diketopiperazines: Isolation, synthesis and optical properties

Article abstract of DOI:10.3987/COM-14-S(K)87

Seven 2,5-diketopiperazines (DKPs) were isolated from the Fijian marine sponge Acanthella cavernosa. NMR and circular dichroism (CD) comparison with synthetic L-L DKPs allowed us to determine unambiguously the L-L absolute configuration of the natural DKPs. This work initiated the setting up of an optical properties database of natural DKPs, including specific rotation and CD.

Full text of DOI:10.3987/COM-14-S(K)87

Supporting information:
MARINE NATURAL OCCURRING 2,5-
DIKETOPIPERAZINES: ISOLATION, SYNTHESIS AND
OPTICAL PROPERTIES
Rémi Laville,1 Thanh Binh Nguyen,1 Céline Moriou,1 Sylvain
Petek,2 Cécile Debitus,2 and Ali Al-Mourabit*1
1
Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des
Substances Naturelles, CNRS, 91198, Gif-sur-Yvette Cedex, France. 2
IRD, UMR241, centre de Polynésie française, BP529, Papeete, French
Polynesia, France.
e-mail: ali.al-mourabit@icsn.cnrs-gif.fr.

S1. 1H NMR spectra of natural and synthetic cyclo(L-Phe-L-Leu) (1) in MeOD (500 MHz)
S2. DEPT135 13C NMR of natural cyclo(L-Phe-L-Leu) (1) in MeOD (150 MHz)
1
S3. H NMR spectra of natural and synthetic cyclo(L-Phe-L-iLeu) (2) in MeOD (500 MHz)
S4. 13C NMR spectra of natural and synthetic cyclo(L-Phe-L-iLeu) (2) in MeOD (125 MHz)
S5. 1H NMR spectra of natural and synthetic cyclo(L-Phe-L-Val) (3) in MeOD (500 MHz)
S6. 13C NMR spectra of natural and synthetic cyclo(L-Phe-L-Val) (3) in MeOD (125 MHz)
S7. 1H NMR spectra of natural and synthetic cyclo(L-Tyr-L-iLeu) (4) in MeOD (500 MHz)
S8. 1H NMR spectra of natural cyclo(L-Tyr-L-iLeu) (4) in DMSO (500 MHz)
S9. 13C NMR spectra of synthetic cyclo(L-Tyr-L-iLeu) (4) in MeOD (125 MHz)
S10. 1H NMR spectra of natural and synthetic cyclo(L-Leu-L-iLeu) (5) in MeOD (500 MHz)
S11. 13C NMR spectra of natural and synthetic cyclo(L-Leu-L-iLeu) (5) in CDCl3 (125 MHz)
S12. 1H NMR spectra of natural and synthetic cyclo(L-Phe-L-Thr) (6) in MeOD (500 MHz)
S13. 13C NMR spectra of natural and synthetic cyclo(L-Phe-L-Thr) (6) in MeOD (125 MHz)
S14. 1H NMR spectra of natural and synthetic cyclo(L-Phe-L-Tyr) (7) in DMSO (500 MHz)
S15. 13C NMR spectra of natural and synthetic cyclo(L-Phe-L-Tyr) (7) in DMSO (500 MHz)
S16. Molecular Circular Dichroism spectra of cyclo(L-Phe-L-Leu) (1) in MeOH (10-5 M)
S17. Molecular Circular Dichroism spectra of cyclo(L-Phe-L-iLeu) (2) in MeOH (10-5 M)
S18. Molecular Circular Dichroism spectra of cyclo(L-Phe-L-Val) (3) in MeOH (10-5 M)
S19. Molecular Circular Dichroism spectra of cyclo(L-Tyr-L-iLeu) (4) in MeOH (10-5 M)
S20. Molecular Circular Dichroism spectra of cyclo(L-Leu-L-iLeu) (5) in MeOH (10-5 M)
S21. Molecular Circular Dichroism spectra of cyclo(L-Phe-L-Thr) (6) in MeOH (10-5 M)
S22. Molecular Circular Dichroism spectra of cyclo(L-Phe-L-Tyr) (7) in MeOH (10-5 M)

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Natural
Synthetic
S1. 1H NMR spectra of natural and synthetic cyclo(L-Phe-L-Leu) (1) in MeOD (500 MHz)
S2. DEPT135 13C NMR of natural cyclo(L-Phe-L-Leu) (1) in MeOD (150 MHz)

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Natural
Synthetic
S3. 1H NMR spectra of natural and synthetic cyclo(L-Phe-L-iLeu) (2) in MeOD (500 MHz)
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Natural
Synthetic
S4. 13C NMR spectra of natural and synthetic cyclo(L-Phe-L-iLeu) (2) in MeOD (125 MHz)

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Natural
Synthetic
S5. 1H NMR spectra of natural and synthetic cyclo(L-Phe-L-Val) (3) in MeOD (500 MHz)
S6. 13C NMR spectra of natural and synthetic cyclo(L-Phe-L-Val) (3) in MeOD (125 MHz)

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Natural
Synthetic
S7. 1H NMR spectra of natural and synthetic cyclo(L-Tyr-L-iLeu) (4) in MeOD (500 MHz)
S8. 1H NMR spectra of natural cyclo(L-Tyr-L-iLeu) (4) in DMSO (500 MHz)

S9. 13C NMR spectra of synthetic cyclo(L-Tyr-L-iLeu) (4) in MeOD (125 MHz)

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Natural
Synthetic
S10. 1H NMR spectra of natural and synthetic cyclo(L-Leu-L-iLeu) (5) in MeOD (500 MHz)
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Natural
Synthetic
S11. 13C NMR spectra of natural and synthetic cyclo(L-Leu-L-iLeu) (5) in CDCl3 (125 MHz)

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Natural
Synthetic
S12. 1H NMR spectra of natural and synthetic cyclo(L-Phe-L-Thr) (6) in MeOD (500 MHz)
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Natural
Synthetic
S13. 13C NMR spectra of natural and synthetic cyclo(L-Phe-L-Thr) (6) in MeOD (125 MHz)

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Natural
Synthetic
S14. 1H NMR spectra of natural and synthetic cyclo(L-Phe-L-Tyr) (7) in DMSO (500 MHz)
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Natural
Synthetic
S15. 13C NMR spectra of natural and synthetic cyclo(L-Phe-L-Tyr) (7) in DMSO (500 MHz)

S16. Molecular Circular Dichroism spectra of cyclo(L-Phe-L-Leu) (1) in MeOH (10-5 M)
S17. Molecular Circular Dichroism spectra of cyclo(L-Phe-L-iLeu) (2) in MeOH (10-5 M)

S18. Molecular Circular Dichroism spectra of cyclo(L-Phe-L-Val) (3) in MeOH (10-5 M)
S19. Molecular Circular Dichroism spectra of cyclo(L-Tyr-L-iLeu) (4) in MeOH (10-5 M)

S20. Molecular Circular Dichroism spectra of cyclo(L-Leu-L-iLeu) (5) in MeOH (10-5 M)
S21. Molecular Circular Dichroism spectra of cyclo(L-Phe-L-Thr) (6) in MeOH (10-5 M)

S22. Molecular Circular Dichroism spectra of cyclo(L-Phe-L-Tyr) (7) in MeOH (10-5 M)