HiPep Laboratories, Nakatsukasacho 486-46, Kamigyo-ku, Kyoto, Japan.
Amino Acids. 2012 Jul;43(1):475-82. doi: 10.1007/s00726-011-1104-y. Epub 2011 Oct 13.
Focusing on drug discovery non-proteinogenic amino acids have often been used as important building blocks for construction of compound libraries in the filed of combinatorial chemistry and chemical biology. Highly homogeneous L: -mimosine, α-amino-β-(3-hydoxy-4-oxo-1,4-dihydropyridin-1-yl)-propanoic acid, a non-proteinogenic amino acid, has been successfully isolated and purified on an industrial scale from wild leaves of Leucaena (Leucaena leucocephala de Wit) which is a widely distributed legume in Okinawa, a sub-tropical island in Japan. Optical purity determinations used for quality control have been established through diastereomer formation. Physico-chemical properties and biological properties of purified mimosine have been clarified. Mimosine is sparingly soluble in water and organic solvents but can be dissolved in aqueous alkaline solution. The tyrosinase pathway is of particular interest in the cosmetic field, since mimosine is an analog of tyrosine. Thus the present purified mimosine have been tested in tyrosinase inhibitory assays. The IC50 for tyrosinase inhibitory activity of purified Mim was compared with kojic acid. Mimosine shows significant inhibition of melanin production in murine melanoma cells. The derivatization of mimosine has been investigated with a focus on its use in conventional peptide syntheses to generate mimosyl peptides. N-(9-Fluorenylmethoxycarbonyloxy)-mimosine and resin-bound mimosine for solid-phase syntheses have also been performed. Highly homogeneous Mim is a useful material for the development of functional cosmetics or active pharmaceutical ingredients.
专注于药物发现，非蛋白氨基酸经常被用作组合化学和化学生物学领域构建化合物库的重要构建块。高度均一的 L: -mimosine，α-氨基-β-(3-羟基-4-氧代-1,4-二氢吡啶-1-基）-丙酸，一种非蛋白氨基酸，已经成功地从 Leucaena（Leucaena leucocephala de Wit）的野生叶子中分离和纯化，Leucaena 是一种广泛分布在日本冲绳亚热带岛屿上的豆科植物。用于质量控制的光学纯度测定已经通过非对映异构体形成建立。纯化的 mimosine 的物理化学性质和生物学性质已经得到阐明。Mimosine 在水中和有机溶剂中的溶解度较低，但可以在碱性水溶液中溶解。由于 mimosine 是酪氨酸的类似物，因此酪氨酸途径在化妆品领域特别有趣。因此，目前已经对纯化的 mimosine 进行了酪氨酸酶抑制试验。与 kojic 酸相比，纯化 Mim 的酪氨酸酶抑制活性的 IC50。Mimosine 显示出对鼠黑色素瘤细胞中黑色素生成的显著抑制作用。已经研究了 mimosine 的衍生化，重点是其在常规肽合成中的用途，以生成 mimosyl 肽。也进行了 N-(9-芴甲氧羰基氧基）-mimosine 和树脂结合的 mimosine 用于固相合成。高度均一的 Mim 是开发功能性化妆品或活性药物成分的有用材料。
