L-ビオプテリン 化学特性,用途語,生産方法
解説
L-エリスロ体は淡黄色の微結晶．分解点250～280 ℃．[α]D"－50°(0.1 mol dm－3 塩酸)．λmax 267，423 nm(ε 16.1×103，10.3×103，pH 5)．pKa1 2.23，pKa2 7.89．酸，アルカリに易溶，水に微溶，有機溶媒に不溶．原虫Crithidia fasciculataの生育促進作用がある．
森北出版「化学辞典（第2版）
製造
最初，ヒトの尿から単離されたが，微生物，昆虫，藻類，両生類の皮膚，ロイヤルゼリーなど自然界に広く分布している．
説明
6-Biopterin (L-Biopterin) is the oxidized form of tetrahydro-L-biopterin (BH4), a nitric oxide synthase (NOS) cofactor. L-Biopterin can be reduced to BH4 via thioredoxin reductase followed by dihydropteridine reductase or reduced glutathione. It is extremely toxic to human melanocytes in culture (IC50 = 0.2 μM after 48 hrs). L-Biopterin is rarely found under physiological conditions except in the epidermis of patients with the depigmentation disorder Vitiligo.
化学的特性
Crystalline Solid
使用
L-Biopterin is a pteridine widely distributed in nature; naturally occurring as the L-erythro-form. Considered as a growth factor for some insects. Fluoresces with a blue color in alkaline solution.
製造方法
Biopterin is synthesized by reacting 2,4,5-triamino-6-hydroxypyrimidine with 5-deoxy-L-arabinosone in aqueous solution at pH of about 7.5 to 10, acidifying and then recrystallizing by dissolving in basic solution and precipitating with acid. 5-deoxy-L-arabinosone is prepared by oxidizing S-deoxy-L-arabinose, which is prepared from L-rhamnose, using cupric acetate.
Process for the synthesis of biopterin
定義
6-Biopterin is an enzymatic cofactor derived from pterin and involved in certain oxidation-reduction reactions. It is a biopterin in which the 1,2-dihydroxypropyl group has (1R,2S)-configuration; naturally occurring form. It is an enantiomer of a D-erythro-biopterin.
主な応用
6-Biopterin is an oxidation product from the melanogenesis regulating cofactor (6R)5,6,7,8 tetrahydrobiopterin (6-BH4). In vitro, 6-Biopterin is cytotoxic to melanocytes. However, in vivo, 6-Biopterin is rapidly and sequentially reduced back to 6-GH4 via q-BH2. Recent studies suggest that 6-Biopterin among other pteridines may be a useful non-invasive biomarker for cancer.
安全性プロファイル
Moderately toxic by ingestion andintraperitoneal routes. Mutation data reported. Whenheated to decomposition it emits toxic vapors of NOx.
L-ビオプテリン 上流と下流の製品情報
原材料
準備製品