Synthesis of a Macrocycle Based on Linked Amino Acid Mimetics (LAAM)

Tetrahedron Lett. 2013 Oct 23;54(43):5799-5801. doi: 10.1016/j.tetlet.2013.08.041.

Abstract

We report the synthesis of a macrocycle utilizing a novel framework of standard amino acids in combination with subunits that we have named as Linked Amino Acid Mimetics (LAAM's). Macrocycles based on the LAAM concept provide both a peptide targeting region and two independently variable functional regions. In the prototype structure, the commonly known Arg-Gly-Asp (RGD) sequence was used for the targeting region. The functional regions contain a phenyl group, and the linkage was formed via a Ring-Closing Metathesis (RCM) reaction.