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  • 4-Substituted boro-proline dipeptides: synthesis, characterization, and dipeptidyl peptidase IV, 8, and 9 activities.

4-Substituted boro-proline dipeptides: synthesis, characterization, and dipeptidyl peptidase IV, 8, and 9 activities.

Bioorganic & medicinal chemistry letters (2012-08-03)
Wengen Wu, Yuxin Liu, Lawrence J Milo, Ying Shu, Peng Zhao, Youhua Li, Iwona Woznica, Gengli Yu, David G Sanford, Yuhong Zhou, Sarah E Poplawski, Beth A Connolly, James L Sudmeier, William W Bachovchin, Jack H Lai
PMID22853995
ABSTRACT

The boroProline-based dipeptidyl boronic acids were among the first DPP-IV inhibitors identified, and remain the most potent known. We introduced various substitutions at the 4-position of the boroProline ring regioselectively and stereoselectively, and incorporated these aminoboronic acids into a series of 4-substituted boroPro-based dipeptides. Among these dipeptidyl boronic acids, Arg-(4S)-boroHyp (4q) was the most potent inhibitor of DPP-IV, DPP8 and DPP9, while (4S)-Hyp-(4R)-boroHyp (4o) exhibited the most selectivity for DPP-IV over DPP8 and DPP9.