Syntheses of New Arginine Derivatives as a Substrate for Trypsin or Papain

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Two new enzymic substrates, tosyl-L(D or DL)-arginine-p-nitroanilide (L-TAPA, D-TAPA, and DL-TAPA) and acetyl-L(D or DL)-arginine-p-nitroanilide (L-AAPA, D-AAPA, and DL-AAPA) were synthesized by the route for benzoyl-L-arginine-p-nitroanilide (L-BAPA) reported previously. The previous method for synthesis of L-BAPA was then improved by the direct benzoylation of L-arginine-p-nitroanilide dihydrochloride (L-APA), into which Nα-benzyloxycarbonyl-Nω-nitro-L-arginine-p-nitroanilide was converted by the simultaneous removal of benzyloxycarbonyl and nitro groups with hydrogen fluoride. This route has the advantages of shorter reaction steps and a better over-all yield than in the case of the previous method. The method is also applicable to the synthesis of L(D or DL)-AAPA, but it is hard to prepare L(D or DL)-TAPA by the method.
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