Kasumigamide, an antialgal peptide from the cyanobacterium Microcystis aeruginosa

Journal of Organic Chemistry

Volumn 65, Issue 19, 2000, Pages 5898-5900

  Ishida, Keishi ^a   Murakami, Masahiro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KASUMIGAMIDE; PEPTIDE DERIVATIVE; TETRAPEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; CHLAMYDOMONAS; GREEN ALGA; MARINE ENVIRONMENT; MICROCYSTIS AERUGINOSA; NONHUMAN; PROTEIN ISOLATION; SEA; STEREOCHEMISTRY;

ALGAE, GREEN; AMINO ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; MICROCYSTIS; OLIGOPEPTIDES; PESTICIDES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 0034703342     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991918f     Document Type: Article

References (15)

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6. 9, Δ +3.2 mmu). Kasumigamide (115.7 mg) was also obtained from freeze-dried alga (116 g) of M. aeruginosa TAC-91 in our laboratory.
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9. erythro-β-Phenyl-D,L-serine was prepared from threo-β-phenyl-D,L-serine. (a) Bolhofer, W. A. J. Am. Chem. Soc. 1952, 74, 5459-5461.
10. 25D (2% solution in 6 N HCl) threo-β-phenyl-L-serine, - 48.6°; threo-β-phenyl-D-serine, + 48.0°; erythro-β-phenyl-L-serine, + 81.3°; erythro-β-phenyl-D-serine, -82.0°].
11. For experimental details of the synthetic procedures, see Supporting Information. β-Phenylserine was derivatized with L-Marfey's reagent and analyzed by reversed-phase HPLC (Cosmosil 5C18-MS, 4.6 × 250 mm; 35% MeCN containing 0.1% TFA; UV detection 340 nm; flow rate 1.0 mL/min). Retention times in the derivatives of the standards (min): erythro-β-phenyl-L-serine (14.8), threo-β-pheny]-L-serine (15.6), erythro-β-phenyl-D-serine (19.2), threo-β-phenyl-D-serine (24.8). Retention time in the derivatives of β-phenylserine of 1 (min): (19.2).
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14. 6 and analyzed by reversed-phase HPLC (Cosmosil 5C18-MS, 4.6 × 250 mm, 20-60% (1%/min) MeCN containing 0.05% TFA, UV detection 340 nm, flow rate 1.0 mL/min). Retention times (min) of standards: (3R,4S)-Ahipa (28.8), (3S,4S)-Ahipa (29.4), (3S,4R)-Ahipa (30.6), (3R,4R)-Ahipa (32.0), derivative from 1 (30.6).
15. 2Ar), 3.15 (br, 1H, CH), 3.71 (m, 1H, CHOH), 6.97 (t, 8.1, 1H, ind.), 7.06 (t, 8.1, 1H, ind.), 7.20 (s, 1H, ind.), 7.34 (d, 8.1, 1H, ind.), 7.54 (d, 8.1, 1H, ind.), 10.88 (s, 1H, NH).