Amino Acids and Peptides. XXXV. Facile Preparation of p-Nitroanilide Analogs by the Solid-Phase Method.

Selection of New Chromogenic Substrates of Serine Proteinases Using Combinatorial Chemistry Methods

“…Anb 5,2 can be considered as a pNA analogue containing an additional carboxyl moiety attached to the benzene ring; this additional functional group can be easily utilized as a linker anchoring the peptide molecule to the polymer. As reported by the Japanese group, Anb 5,2 and pNA possess the same spectral characteristics [12]. In our recent work, we have shown that the peptide library with Anb 5,2 can be used for designing and selecting potent trypsin chromogenic substrates [13].…”

“…The amino acid -amino groups were protected by a fluorenylo-9-metoxycarbonyl (Fmoc-) moiety. 5-Amino-2-nitrobenzoic acid was attached to the resin using the TBTU/DMAP method [12]. The C-terminal amino acid residues were incorporated using POCl 3 as the coupling reagent [12].…”

“…Sobieskiego 18, 80-952 Gda sk, Poland; E-mail: adas@chem.univ.gda.pl In order to overcome this problem, Hojo et al [12] introduced 5-amino-2-nitrobenzoic acid (Anb 5,2 ) at the C-termini of the synthesized peptides. Anb 5,2 can be considered as a pNA analogue containing an additional carboxyl moiety attached to the benzene ring; this additional functional group can be easily utilized as a linker anchoring the peptide molecule to the polymer.…”

Design and synthesis of new substrates of HtrA2 protease

“…In order to achieve a complete resin substitution with ANB the coupling procedure was repeated three times. Next, the first Fmoc-protected amino acid was conjugated to ANB using a POCl 3 /pyridine system [13]. The following Fmoc deprotection steps were performed using 20% piperidine in DMF/NMP whereas all the subsequent Fmoc-protected amino acids were conjugated using the DIPCI/HOBt coupling system.…”

An efficient Fmoc strategy for the rapid synthesis of peptide para-nitroanilides

“…A survey of the literature revealed only a few reasonably general solid-phase strategies for peptide p-nitroanilide synthesis [3][4][5][6][7][8]. Of these, three were directly applicable to the problem at hand.…”