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Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound |
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| Authors: | Mira S Bjelakovi? Natalija M Krsti? Milan M Dabovi? Martin Kessler Vladimir D Pavlovi? |
| Institution: | a Center for Chemistry, ICTM, Studentski trg 12-16, PO Box 473, 11001 Belgrade, Serbia b Departments of Biochemistry and Molecular Biology, Mayo College of Medicine, Mayo Clinic and Foundation, Rochester, MN 55905, USA c Novartis Pharma AG, Lichtstrasse 35, CH-4056 Basel, Switzerland d Leimgrubenweg 21, CH-4102 Binningen, Switzerland e Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, PO Box 158, 11001 Belgrade, Serbia |
| Abstract: | We report herein the synthesis of a novel modified steroid with two rigidly positioned amino acids in C- and N-protected forms (Gly-OtBu and N-Fmoc-l-Phe) at the angular positions (C-18 methylamino group and C-19 carboxylic function) of the steroid nucleus via amide bonds, starting from 18-cyanopregnenolone acetate over 10 steps. In an attempt to gain more insight into the structural and conformational features of this novel 18-Phe,19-Gly-containing steroidal compound, we describe the detailed 2D NMR spectral analysis. Despite the large size and the conformational flexibility of the amino acid units in this molecule, conformational analysis by NOESY connectivities showed the existence of mainly one conformation (∼95%) in CDCl3 solution with approximately parallel orientation of the phenylalanine and glycine moieties. |
| Keywords: | STAP concept 18-Phe 19-Gly-containing steroidal compound 2D NMR analysis 18-Cyanopregnenolone acetate |
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