Anabaenopeptins G and H, potent carboxypeptidase A inhibitors from the cyanobacterium Oscillatoria agardhii (NIES-595)

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 9, 1999, Pages 1243-1246

  Itou, Yusai ^a   Suzuki, Shingo ^a   Ishida, Keishi ^a   Murakami, Masahiro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANABAENOPEPTIN G; ANABAENOPEPTIN H; BACTERIAL TOXIN; CARBOXYPEPTIDASE A; UNCLASSIFIED DRUG;

ANABAENA; ARTICLE; CHEMICAL ANALYSIS; CHROMATOGRAPHY; CYANOBACTERIUM; ENZYME INHIBITOR INTERACTION; INHIBITION KINETICS; NUCLEAR MAGNETIC RESONANCE; PROTEIN ANALYSIS; PROTEIN ISOLATION; PROTEIN STRUCTURE; SPECTROSCOPY; STRUCTURE ANALYSIS;

CARBOXYPEPTIDASES; CARBOXYPEPTIDASES A; CYANOBACTERIA; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES, CYCLIC;

EID: 0033519245     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00191-2     Document Type: Article

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8. 18 MS column, 4.6 × 250 mm; 0-60% MeCN containing 0.1% TFA in 60 min; flow rate 1 mL/min, UV detection at 340 nm). The identity of each peak was confirmed by coinjection with a solution of a standard that had been derivatized in the same manner, but L-Hty-D-FDAA derivative was substituted for D-Hty- L-FDAA derivative. Retention times (min): D-Lys (34.6), D-Arg (35.6), L-Lys (36.0), L-Arg (36.8), L-Ile (50.2), D-Ile (54.4), L- Hty (62.8), D-Hty (65.2). In order to separate N-Me-D,L-Glu clearly, an isocratic elution (20% MeCN containing 0.1% TFA) was used. Retention times (min): N-Me-D-Glu (42.8), N-Me-L-Glu (45.6).
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10. 13C NMR data δ (mult., carbon position), Ile (1) [170.6 (s, C-1), 59.3 (d, C-2), 35.9 (d, C-3), 23.8 (t, C-4), 11.2 (q, C-5), 15.8 (q, C-6)], N-Me-Hty [169.3 (s, C-1), 59.3 (d, C-2), 30.7 (t, C-3), 31.4 (t, C-4), 131.5 (s, C-5), 128.9 (d, C-6,10), 115.2 (d, C-7,9), 155.58 (s, C-8), 28.5 (q, N- Me)], Hty [172.3 (s, C-1), 48.1 (d, C-2), 33.1 (t, C-3), 30.7 (t, C-4), 131.0 (s, C-5), 129.3 (d, C-6,10), 115.1 (d, C-7,9), 155.60 (s, C-8)], Ile (2) [172.9 (s, C-1), 55.7 (d, C-2), 36.2 (d, C-3), 25.5 (t, C-4), 11.4 (q, C-5), 14.5 (q, C-6)], Lys [172.2 (s, C-1), 54.9 (d, C-2), 30.7 (t, C-3), 20.2 (t, C-4), 27.9 (t, C-5), 38.0 (t, C-6)], ureido [157.3 (s)], Arg [174.1 (s, C-1), 51.8 (d, C-2), 29.4 (t, C-3), 25.0 (t, C-4), 40.4 (t, C-5), 156.7 (s, C-6)].
11. To test tubes were added: 0.4 mL of 1 M Tris HCl, 0.5 M NaCl, pH 7.5; 1.0 mL of sample solution, 30 μL of methanolic sample with 970 μL of distilled water; 0.1 mL of enzyme (Sigma, ex Bovine pancreas, 0.4 units/mL in 10% LiCl). The tubes were mixed and incubated at 37 °C for 30 min, after which time, 1.5 mL of substrate solution, (hippuryl-L-phenylalanine, 0.55 mg/mL of 1 M Tris HCl, 0.5 M NaCl, pH 7.5) was added. The absorbance of 254 nm of each tube was read immediately, (time 0) and after 2 hours incubation at room temperature.
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