Nagahamide A, an Antibacterial Depsipeptide from the Marine Sponge Theonella swinhoei

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3039-3042

  Okada, Yumika ^a   Matsunaga, Shigeki ^a   Van Soest, Rob W M ^b   Fusetani, Nobuhiro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; CYCLOPEPTIDE; DEPSIPEPTIDE; NAGAHAMIDE A;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ESCHERICHIA COLI; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STAPHYLOCOCCUS AUREUS; STEREOISOMERISM;

ANIMALS; ANTI-BACTERIAL AGENTS; DEPSIPEPTIDES; ESCHERICHIA COLI; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES, CYCLIC; PORIFERA; STAPHYLOCOCCUS AUREUS; STEREOISOMERISM;

EID: 0037026504     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0262791     Document Type: Article

References (14)

1. Bioactive Marine Metabolites. 114. Part 113: Fujita, M.; Nakao, Y.; Matsunaga, S.; Nishikawa, T.; Fusetani, N. Submitted for publication.
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3. The sponge was collected at depths of 3-5 m near Nagahama, Kamikoshiki-jima Island (31° 39.00' N, 129° 44.30' E) in October 1994.
4. Matsunaga, S.; Fusetani, N. J. Org. Chem. 1995, 60, 1177-1181.
5. 13C NMR data, see Table 1.
6. 4
7. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591-596.
8. 4 Both isomers of erythro-β-Me-Asp were prepared as follows. A commercially available diastereomeric mixture of threo- and erythro-β-Me-Asp was converted to a mixture of N-Cbz-di(p-bromophenacyl) ester derivatives, which was separated by silica gel HPLC to afford N-Cbz-di(p-bromophenacyl) ester derivative of erythro-β-Me-DL-Asp. The enatiomeric mixture was separated by HPLC on Chiralcel OJ (EtOH) followed by acid hydrolysis to afford erythro-β-Me-D-Asp and erythro-β-Me-L-Asp, whose configurations were assigned by Marfey's analysis using the D-isomer obtained from the acid hydrolysate of microsystin LR as a standard. AHBA was obtained by acid hydrolysis of (3S)-3-hydroxypyrrolidine-2-one.
9. (a) Shibazaki, M.; Sugawara, T.; Nagai, K.; Shimizu, Y.; Yamaguchi, H.; Suzuki, K. J Antibiot. 1996, 49, 340-344.
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12. H 3.24 (H-7), 1.76 (H-8), 3.35 (H-9), and 0.67 (Me-8).
13. An inhibitory zone of 7 mm was observed when 50 μg of 1 was applied to a 6-mm φ paper disk on an agar plate inoculated with either E. coli or S. aureus. No inhibition was observed against Saccharomyces cerevisiae and Mortierella ramanniana at the same dose.
14. Bewley, C. A.; Debitus, C.; Faulkner, D. J. J. Am. Chem. Soc. 1994, 116, 7631-7636.