5 years ago

The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry–Biology Interface

The Difference a Single Atom Can Make: Synthesis and Design at the Chemistry–Biology Interface
Dale L. Boger
A Perspective of work in our laboratory on the examination of biologically active compounds, especially natural products, is presented. In the context of individual programs and along with a summary of our work, selected cases are presented that illustrate the impact single atom changes can have on the biological properties of the compounds. The examples were chosen to highlight single heavy atom changes that improve activity, rather than those that involve informative alterations that reduce or abolish activity. The examples were also chosen to illustrate that the impact of such single-atom changes can originate from steric, electronic, conformational, or H-bonding effects, from changes in functional reactivity, from fundamental intermolecular interactions with a biological target, from introduction of a new or altered functionalization site, or from features as simple as improvements in stability or physical properties. Nearly all the examples highlighted represent not only unusual instances of productive deep-seated natural product modifications and were introduced through total synthesis but are also remarkable in that they are derived from only a single heavy atom change in the structure.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02088

DOI: 10.1021/acs.joc.7b02088

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