YM-280193
National Institutes of Health
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..................................................................................................................................... iii Acknowledgements..................................................................................................................... ix Preface ....................................................................................................................................... xi Abbreviations ............................................................................................................................xxi Chapter 1: Introduction ................................................................................................................ 1 1.1 Naturally occurring cyclic peptides .................................................................................... 3 1.1.1 Receptor binding ................................................................................................................. 4 1.1.2 Enzymatic degradation ....................................................................................................... 6 1.1.3 Membrane permeability ..................................................................................................... 8 1.2 Aim of present research .................................................................................................. 11 1.3 Peptide synthesis ............................................................................................................ 13 1.3.1 Solution and solid phase peptide synthesis ...................................................................... 13 1.3.2 Peptide bond formation .................................................................................................... 16 1.3.2.1 Carbodiimide coupling reagents ........................................................................................... 17 1.3.2.2 Benzotriazole based coupling reagents ................................................................................ 18 1.4 Head-to-tail cyclisation strategies .................................................................................... 21 1.4.1 Design of linear precursor ................................................................................................. 21 1.4.3 Solid phase head-to-tail cyclisation strategies .................................................................. 25 Chapter 2: Versicoloritides ......................................................................................................... 33 2.