Synthesis of (3<I>S</I>, 4<I>S</I>)- and (3<I>S</I>, 4<I>R</I>)-4-Amino-3-hydroxy-6-methylheptanoic Acid, and Their <I>N</I>-(Acetyl-L-valyl-L-valyl) Derivatives
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概要
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Natural (−)(3<I>S</I>,4<I>S</I>)-4-amino-3-hydroxy-6-inethylheptanoic acid (<B>10a</B>) present in pepstatins, specific inhibitors of acid proteases, and its (+) (3<I>S</I>,4<I>R</I>) diastereomer (<B>10b</B>) were synthesized starting from 3-deoxy-1,2-<I>O</I>-isopropylidene-α-D-<I>erythro</I>-pentodialdo-1,4-furanose (<B>1</B>) through highly stereoselective and stereospecific routes. The partial pep tide of pepstatin Ac, <I>N</I>-(acetyl-L-valyl-L-valyl)-(3<I>S</I>,4<I>S</I>)-4-amino-3-hydroxy-6-methylheptanoic acid (<B>15a</B>) and its (3<I>S</I>,4<I>R</I>) diastereomer (<B>15b</B>) were synthesized <I>via</I> azide-coupling of the <I>t</I>-butyl esters of <B>10a</B> and <B>10b</B> with acetyl-L-valyl-L-valine azide, respectively. Compound <B>15a</B> inhibited proteolysis by pepsin, however, the diastereomer <B>15b</B> showed no inhibition against pepsin.
- 公益社団法人 日本化学会の論文
著者
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Kinoshita Mitsuhiro
Department of Applied Chemistry Engineering Faculty of Keio University
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Aburaki Shinpei
Department of Applied Chemistry, Faculty of Engineering, Keio University
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Hagiwara Akito
Department of Applied Chemistry, Faculty of Engineering, Keio University
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