C-P compounds, biological activities and medical uses.

自Horiguchi和Kandatsu首次分离出天然C-P化合物2-氨基乙基膦酸盐以来，日本开展了大量工作。本课题为期2年，主要研究方向为：(1)C-P化合物的分离鉴定、(2)组织分布、(3)生物活性、(4)生物合成和(5)化学合成。研究结果如下：(1)从原口虫中分离到几种新的C-P鞘糖脂。它们的碳水化合物和低聚糖结构与后口虫不同。糖脂中2-氨基乙基膦酸酯（C-P）和磷酸乙醇胺（C-O-P）各1摩尔，提示了鞘糖脂种的分子进化方式。（主题二）抗磷酸糖脑苷抗血清特异性染色甲壳类动物神经组织。（主题3）从海芋中分离出的C-P鞘糖脂通过与camp依赖性蛋白激酶的催化亚基结合而激活该蛋白激酶。（主题4）克隆了磷霉素合成的关键酶磷酸烯醇丙酮酸（PnPy）磷酸化酶和PnPy脱羧酶基因，克隆了双磷合成C-P-C键的对甲基化酶基因。（主题5）用复杂的方法将糖半缩醛环上的氧替换为磷，合成了许多新的碳磷化合物。其中一些具有生物活性。

Since Horiguchi and Kandatsu first isolated natural C-P compound, 2-aminoethyl-phosphonate, much work has been carried out in Japan. Theme of the present 2-years project were (1) isolation and identification, (2) tissue distribution, (3) biological activities, (4) biosynthesis and (5) chemical synthesis of the C-P compounds.Following results were obtaied : (Theme 1) Several new C-P sphingoglycolipids were isolated from protostomia. Their carbohydrate and oligosaccharide structures were different from those of deuterostomia. A glycolipid had one mole each of 2-aminoethylphosphonate (C-P) and phosphoethanolamine (C-O-P) which suggests a way of molecular evolution of sphingoglycolipid species. (Theme 2) antiphosphonoglycocerebroside antisera specifically stain nervous tissues of crustacea. (Theme 3) C-P sphingoglycolipids isorated from Aplysia activated cAMP-dependent protein kinase by binding to the catalytic subunit of the enzyme. (theme 4) Genes of phosphoenolpyruvic acid (PnPy) phosphomutase and PnPy decarboxylase which were key enzymes for the synthesis of fosfomycin were cloned and a gene of p-methylating enzyme for the synthesis of C-P-C bond of bialaphos was cloned. (Theme 5) Oxygen of hemiacetal ring of sugar was replaced by phosphorus by sophisticated methods and many novel C-P compounds were chemically synthesized. Some of them were biologically active.