Callynormine A, a new marine cyclic peptide of a novel class

Organic Letters

Volumn 6, Issue 15, 2004, Pages 2543-2545

  Berer, Nelly ^a   Rudi, Amira ^a   Goldberg, Israel ^a   Benayahu, Yehuda ^a   Kashman, Yoel ^a  

^a TEL AVIV UNIVERSITY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CALLYNORMINE A; CYCLOPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPONGE (PORIFERA); X RAY DIFFRACTION;

ANIMALS; CALLYSPONGIA; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; KENYA; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES, CYCLIC; STEREOISOMERISM;

EID: 4043119201     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0491787     Document Type: Article

References (15)

1. Faulkner, D. J. Nat. Prod. Rep. 2002, 19, 1-49 and previous reviews in this series.
2. Schemjakin, M. M. Angew Chem. 1960, 72, 342-343.
3. Munro, M. H. G.; Blunt, J. W. Marine Literature Database, Department of Chemistry, University of Canterbury.
4. Fusetani, N.; Matsunaga, S. Chem. Rev. 1993, 93, 1793-1806.
5. Fusetani, N.; Matsunaga, S. Curr. Org. Chem. 2003, 7, 945-966.
6. The nomenclature of amino acids and peptides is located at http://www.chem.qmul.ac.uk/iupac/AminoAcid/.
7. 3. The benzyl group of the phenylalanine fragment was found disordered between two differently oriented and equally probable positions. The acetonitrile crystallization solvent is also affected by partial disorder.
8. Sheldrick, G. M.; SHELXD-97 and SHELXL-97. Programs for the Solution and Refinement of Crystal Structures from Diffraction Data, University of Göttingen, Germany, 1997.
9. Svete, J.; Aljaz-Rozic, M.; Stanovnik, B. J. Heterocycl. Chem. 1997, 34, 177-193.
10. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591-596. L-Pro, L-Phe, and L-Ile were identified by this method.
11. NH[Leu(7)] does not exchange due to a hydrogen bond to CO[Pro(6)] (2.7 Å in the crystal).
12. ROESY correlations between Leu(4) H-2 and NH to Pro(9) H-5 and between Val (3) H-2 to Pro(9) H-2.
13. Dierks, T.; Miech, C.; Hummerjohann, J.; Schmidt, B.; Kertesz, M. A.; von Figura, K. J. Biol. Chem. 1998, 273, 25560-25564.
14. Chruszcz, M.; Laidler, P.; Monkiewicz, M.; Ortlund, E.; Lebioda, L.; Lewinski, K. J. Inorg. Biochem. 2003, 96, 386-392.
15. Singh, R.; Zhou, N.; Reddy, A. V. N.; Thomas, G.; Ding, Q.; Kaleta, J.; Micetich, R. G.; Whittaker, M. US Patent 6,635,621 B1, 2003.