The Cyclo?螃漫?Tetrapeptide (β??HPhe?螃漫?HThr?螃漫?HLys?螃漫?HTrp): Synthesis, NMR Structure in Methanol Solution, and Affinity for Human Somatostatin Receptors

K Gademann, M Ernst, D Seebach…

Index: Gademann, Karl; Ernst, Martin; Seebach, Dieter; Hoyer, Daniel Helvetica Chimica Acta, 2000 , vol. 83, # 1 p. 16 - 33

Full Text: HTML

Citation Number: 92

Abstract

Abstract The known solid-state structure (Fig. 1, top) of cyclo (β-HAla) 4 was used to model the structure of the title compound 1 as a prospective somatostatin mimic (Fig. 1, bottom). The synthesis started with the N-protected natural amino acids Boc-Phe-OH, Boc-Trp-OH, Boc-Lys (2-Cl-Z)-OH, and Boc-Thr (OBn)-OH, which were homologated to the corresponding β-amino-acid derivatives (Scheme 1) and coupled to the β-tetrapeptide Boc-β-HTrp-β- ...