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. Author manuscript; available in PMC: 2009 Sep 28.
Published in final edited form as: J Mol Biol. 2008 Jan 5;376(5):1438–1450. doi: 10.1016/j.jmb.2007.12.066

Figure 1. Chemical formulas of GCPII substrates (Panel A) and phosphinate transition-state analogs thereof (Panel B).

Figure 1

Panel A, folyl-γ-glu, a natural GCPII substrate present in the small intestine; γ-glu-glu; γ-glutamyl-glutamate; NAAG, N-acetyl-aspartyl-glutamate, a dipeptidic natural GCPII substrate in the nervous system. Panel B, MPE, 2-[(3-{4-[(2-amino-4-hydroxy-pteridin-6-ylmethyl)-amino]-benzoylamino}-3-carboxy-propyl)-hydroxy-phosphinoylmethyl]-pentanedioic acid; EPE, (2S,3′S)-{[(3′-Amino-3′-carboxy-propyl)-hydroxyphosphinoyl]methyl}-pentanedioic acid; SPE, (2S)-2-{[(2-carboxy-ethyl)-hydroxy-phosphinoyl]methyl}-pentanedioic acid. Chiral centers are indicated by asterisks, numbers 1 and 1′ mark P1 and P1′ chiral centers, respectively.