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A Practical Synthesis of Gramicidin S and Sugar Amino Acid Containing Analogues

2004; American Chemical Society; Volume: 69; Issue: 23 Linguagem: Inglês

10.1021/jo0487449

1520-6904

Gijsbert M. Grotenbreg, Martijn Kronemeijer, Mattie S. M. Timmer, Farid El Oualid, Renate M. van Well, Martijn Verdoes, Emile Spalburg, Peter A. V. van Hooft, Albert J. de Neeling, Daan Noort, Jacques H. van Boom, Gijsbert A. van der Marel, Herman S. Overkleeft, Mark Overhand,

Glycosylation and Glycoproteins Research

A practical gram-scale and high-yielding synthesis of the antimicrobial peptide gramicidin S is presented. An Fmoc-based solid-phase peptide synthesis protocol is employed for the generation of the linear decapeptide precursor, which is cyclized in solution to afford the target compound. The versatility of our method is demonstrated by the construction of eight gramicidin S analogues (15a−h) having nonproteinogenic sugar amino acid residues (4−7) incorporated in the turn regions.