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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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The solid-phase synthesis of novel 14-membered macrocycles for high throughput screening.

A simple and efficient synthesis of novel 14-membered macrocycles from a resin-bound orthogonally protected lysine residue is described. Reductive alkylation of the lysine alpha-nitrogen introduces the first diversity element. Acylation of the resultant secondary amine with an Fmoc-amino acid introduces the second diversity element providing a resin-bound protected di-peptide precursor. Removal of the Fmoc-group is followed by acylation with a succinic anhydride to introduce the final diversity elements. Removal of the methyltrityl-group from the amino group followed by macrocyclization provides the desired macrocycles, after TFA cleavage, in excellent yield and purity.[1]

References

  1. The solid-phase synthesis of novel 14-membered macrocycles for high throughput screening. Lanter, C.L., Guiles, J.W., Rivero, R.A. Mol. Divers. (1998) [Pubmed]
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