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Identification of the major degradation products of MTX-cIBR at pH 1.0. Pathway a shows the degradation of the MTX portion of the conjugate by clipping the C-N bond between the pteridine ring and the p-amino-benzoyl ring to give compound 2. Pathway b represents demethylation reaction of compound 2 to give degradation product 3. Pathway c shows cleavage between the p-amino-benzoyl group and the Glu residue of the MTX fragment of the conjugate (compound 4).
