alpha-Amido boronic acids: a synthetic challenge and their properties as serine protease inhibitors.

This review includes a personal account of the history of the development of the alpha-amido boronic acid synthesis and related chemistry in the author's laboratory, as well as a review of some of the more significant developments that have occurred elsewhere more recently. The simple initial target, suggested by biochemist G. E. Lienhard, proved much more elusive to reach than anticipated. The circuitous effort that ultimately revealed the deceptively simple successful route, for which there is still no alternative, will be described. The properties of these compounds as enzyme inhibitors will be described very briefly. More extensive reviews of the enzyme inhibiting properties of alpha-amido boronic acids have appeared recently. (c) 2007 Wiley Periodicals, Inc.