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Eric Biron, Jayanta Chatterjee, Oded Ovadia, Daniel Langenegger, Joseph Brueggen, Daniel Hoyer, Herbert A. Schmid, Raz Jelinek, Chaim Gilon, Amnon Hoffman and Horst Kessler Improving Oral Bioavailability of Peptides by Multiple N-Methylation: Somatostatin Analogues Angewandte Chemie International Edition 47

Article first published online: 22 FEB 2008 | DOI: 10.1002/anie.200705797

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Full methyl jacket? A complete library of the N-methylated somatostatin cyclopeptidic analogue Veber–Hirschmann peptide cyclo(-PFwKTF-) has been prepared with the aim of improving its bioavailability. Several analogues from the library were found to bind to the somatostatin receptor in the nanomolar range and one of them shows a significant oral bioavailability of 10 %. Conformational analysis shows that N-methylation is allowed at specific positions without affecting the bioactive conformation.

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