The Synthesis of Benzoyl-L-arginine-p-nitroanilide

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Benzoyl-arginine-p-nitroanilide (BAPA) is a synthetic substrate for trypsin, papain, and other enzymes, but it has not yet been prepared in the active L-form, although the preparations of DL-form and D-form by the trypsin digestion of the DL-form have been reported. The optically active L-BAPA was prepared by the following route; Nα-carbobenzyloxy-Nω-nitro-L-arginine-p-nitroanilide was prepared from Nα-carbobenzyloxy-Nω-nitro-L-arginine and p-nitrophenyl isocyanate, and the subsequent decarbobenzyloxylation and the benzoylation of this compound gave Nα-benzoyl-Nω-nitro-L-arginine-p-nitroanilide. The removal of the nitro group was followed by Sakakibara's method using hydrogen fluoride. The L-BAPA shows the same melting point and the same reversal optical rotation as those of D-BAPA. When Nα-benzoyl derivatives of L-arginine were used as starting materials in the preparation of BAPA, DL-BAPA was always obtained with complete racemization; when Nα,Nω,Nω′-tricarbobenzyloxy-L-arginme as the starting material reacted on p-nitrophenyl isocyanate, the product had no racemization, but the desired L-BAPA was not obtained because one of the carbobenzyloxy groups on the guanido group was extraordinally stable to reagents and could not be removed completely.
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