Enzymatic Synthesis of Dehydro Cyclo(His-Phe)s, Analogs of the Potent Cell Cycle Inhibitor, Dehydrophenylahistin, and Their Inhibitory Activities toward Cell Division

概要

論文の詳細を見る
Cyclo(His–Phe) was effectively converted to its dehydro derivatives by the enzyme of Streptomyces albulus KO-23, an albonoursin-producing actinomycete. Two types of dehydro derivatives were isolated from the reaction mixture and identified as cyclo(ΔHis–ΔPhe) and cyclo(His–ΔPhe). This is the first report on cyclo(His–ΔPhe) and the enzymatic preparation of both compounds. Cyclo(ΔHis–ΔPhe), a tetradehydro cyclic dipeptide, exhibited a minimum inhibitory concentration of 0.78 μmol/ml inhibitory activity toward the first cleavage of sea urchin embryos, in contrast to cyclo(His–ΔPhe) that had no activity. The finding that the isoprenylated derivative of cyclo(ΔHis–ΔPhe), dehydrophyenylahistin, had 2,000 times higher activity than cyclo(ΔHis–ΔPhe) indicates that an isoprenyl group attached to an imidazole ring of the compound was essential for the inhibitory activity.
社団法人日本農芸化学会の論文
2004-11-23