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. Author manuscript; available in PMC: 2015 Jun 19.
Published in final edited form as: J Pharm Sci. 2012 Apr 26;101(9):3275–3291. doi: 10.1002/jps.23164

Figure 10.

Figure 10

The disulfide bond degradation in MTX-cIBR at pH 12 produced thiolate-sulfenic acid 8 and cyclic dimer 10. The disulfide bond opening was via direct attack of hydroxyl anion on the sulfur of the disulfide bond. Thiolate 8 was reacted with another molecule of the conjugate to produce a linear dimer 9; intramolecular reaction of thiolate anion with the sulfur atom of sulfenic acid generated a cyclic dimer 10.