72(P53) 藍藻Microcystis aeruginosaの生物活性ペプチドの立体化学(ポスター発表の部)
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In the continuous studies of protease inhibitors of microalgae, we have reported that the isolation and structure determination of protease inhibitory peptides. Among these peptides, aeruginosin-type peptides, which were trypsin, plasmin and thrombin inhibitors, were consisted of four units, viz., Hpla (p-hydroxyphenyllactic acid) derivatives, usual amino acids, Choi (2-carboxy-6-hydroxy octahydroindole) derivatives and Arg derivatives. However, the absolute stereochemistry of several units containing Choi in 1-3 and 5 has not been determined. To research new aeruginosin-type peptides, further investigation on the extracts of M. aeruginosa led to the isolation of four new congeners (4 and 6-8). Here we describe the stereochemistry of these peptides, together with the structure determination of the anti-green algal peptide kasumigamide (9). The stereochemistries of the Hpla, chloro Hpla (chloro Hpla sulfate), bromo Hpla and dichloro Hpla units in 1-9 were determined to be D-form by ODS HPLC analyses of menthyl esters of the acid hydrolysates. Standard optically active Hpla was synthesized from p-aminophenylalanine. Chloro and dichloro Hpla were synthesized from Hpla using SO_2Cl_2. Bromo Hpla was synthesized from Hpla using dioxane dibromide. The absolute stereochemistry of the Choi sulfate unit in 1 was determined as follows. The stereochemistry at C-2 of the Choi sulfate unit was determined to be S configuration by NMR analysis of the (R)- and (S)-PGME amides of Choi diacetate (Fig. 1). The relative stereochemistry of the Choi sulfate unit in 1 was decided as shown in Fig. 2 by NOESY correlations and coupling constants. The stereochemistry of the Choi sulfate unit in 1 was 2S, 3'R, 6S, 7'R from these results. The stereochemistry of the argininol unit in 5 was determined as L-form by the HPLC analysis of the Marfey derivatives. L-Argininol was prepared from Boc L-Arg (NO_2) as previously described by Hamada et al. The stereochemistry of the argininal units in 7 and 8 were determined to be 2S and 15, 3R, respectively, by a combination of the HPLC analyses of the Marfey derivatives of oxyproducts of these peptides and NOESY correlations shown in Fig. 3. Kasumigamide (9), an anti-green algal peptide, was isolated from the cyanobacterium M. aeruginosa (NIES-87). Its structure was determined to be a linear tetrapeptide consisting of D-phenyllactic acid, β-Ala, (3S,4R)-4-amino-3-hydroxy-5-indolylpentanoic acid, D-Arg and erythro β-phenyl-D-serine, by a combination of spectral and chemical studies.
- 天然有機化合物討論会の論文
- 1999-09-01
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