67(P-24) 藍藻Microcystis aeruginosaが産生するzinc metalloprotease阻害物質microginin類に関する研究(ポスター発表の部)

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In the continuous studies of protease inhibitors of cyanobacteria, we have reported that the isolation and structure determination of protease inhibitory peptides. Among these peptides, microginin-type peptides, which were aminopeptidase M (APM) and angiotensin-converting enzyme (ACE) inhibitors from the cyanobacterium Microcystis aeruginosa, were linear tetra to hexa-peptides containing Ahda (3-amino-2-hydroxydecanoic acid) derivatives at C-terminus. Here we report the absolute stereochemistry of eight new microginin-type peptides (1-8), together with the structure-activity relationship within a series of degradation and derivative products of microginin (11). The absolute stereochemistry of the MeAhda unit in 1 was determined to be 2S, 3S by a combination of the modified Mosher methods and NOESY correlations of acetonide (9). The correspondence of ^1H and ^<13>C NMR signals of the MeAhda units of 1 and 3 indicated that the stereochemistry of the MeAhda unit of 3 was also 2S, 3S. The absolute stereochemistry of the Ahda unit in 2 was determined to be 2S, 3S by a combination of chemical data of Ahda isolated from the acid hydrolysate of 2 and the coupling constant of oxazolidinone ring protons of 10. The absolute stereochemistry of the dichloro Ahda unit in 8 was also determined to be 2R, 3R by the above-mentioned procedure. The similarity of ^1H and ^<13>C NMR data among the Ahda (halogenated Ahda) units in 4 to 8 indicated that the stereochemistry of the Ahda (halogenated Ahda) units in 4 to 7 were also 2R, 3R. The APM inhibitory mechanism of microginin-type peptides might be same as that of probestin and amastatin, because the structure of microginin-type peptides resembles probestin and amastatin. The structure-activity relationship within a series of degradation and derivative products of microginin indicated that not only the dityrosine unit but also the amino and hydroxyl groups of Ahda play an important role in ACE inhibition of microginin-type peptides.
天然有機化合物討論会の論文
2001-09-01

67(P-24) 藍藻Microcystis aeruginosaが産生するzinc metalloprotease阻害物質microginin類に関する研究(ポスター発表の部)

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