- A convenient synthesis of amino acid p-nitroanilides; synthons in the synthesis of protease substrates
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A method is described for the synthesis of N(α)-protected bi- and trifunctional amino acid p-nitroanilides. The reaction uses phosphorus oxychloride as the condensing agent. The synthesis is simple, rapid, free of racemization and affords yields between 70-90%. The synthesis can be performed not only with amino acid derivatives of the urethane type including acid-labile (Z, Boc) and base-labile (Fmoc, Msc) N(α)-protective functions or allyl-derived protections, but also with N(α)-trityl amino acids, albeit in lower yield. The reaction runs in pyridine and its mechanism implies carboxyl activation by formation of a mixed anhydride with phosphorodichloridic acid (HOPOCl2).
- Rijkers, Dirk T. S.,Adams, Hans P. H. M.,Hemker, H. Coenraad,Tesser, Godefridus I.
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p. 11235 - 11250
(2007/10/02)
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- THE USE OF PHOSPHORUS OXYCHLORIDE IN THE SYNTHESIS OF AMINO ACID p-NITROANILIDES
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Phosphorus oxychloride is described as a condensing agent in the preparation of nitroanilides.The condensation was free of racemization with amino acid derivatives of the urethane type and the current amino protective groups can be applied.The yields are high to excellent.
- Rijkers, D. T. S.,Hemker, H. C.,Nefkens, G. H. L.,Tesser, G. I.
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p. 347 - 348
(2007/10/02)
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- Reinvestigation of the Phosphazo Method and Synthesis of N-(t-Butoxycarbonyl)-L-arginine p-Nitroanilide and a Chromogenic Enzyme Substrate for the Factor Xa
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Reaction conditions for the phosphazo method were reinvestigated in order to apply this method to the synthesis of p-nitroanilide(pNA)s of t-butoxycarbonyl(Boc)- and benzyloxycarbonyl(Z)-amino acids.
- Oyamada, Hidekazu,Saito, Takashi,Inaba, Shinsaku,Ueki, Masaaki
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p. 1422 - 1424
(2007/10/02)
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