2 ヘパリンの蛋白(AT-III)高親和性フラグメントの合成 : 二糖シントンの活用

概要

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One of the most remarkable characteristic of heparin is the high ability as a blood-anticoagulant, which is ascribed to the specific affinity of this mucosaccharide for antithrombin III (AT-III), an inhibitory protein against a series of blood-clotting enzymes. The complex pentasaccharide (1) is the AT-III-binding sequence of heparin recently proposed. This paper describes the synthesis of 1, utilizing cellobiose (6) as a main starting material. The synthetic strategy was built upon the methodology, established by us, for completely regioselective modification of cellobiose (6). Thus, two different disaccharide segment (4 and 5) were prepared from 6, and coupled each oter. The resulting tetrasaccharide (39) was elongated by condensation with the known monosaccharide derivative (3), giving the expected pentasaccharide (2). These syntheses included several key steps such as the configurational inversion from D-gluco to L-ido in the nonreducing end of a disaccharide derivative.
天然有機化合物討論会の論文
1985-09-07