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.
TY - JOUR
AU - Bjelaković, Mira
AU - Krstić, Natalija
AU - Juranić, Nenad
AU - Dabović, Milan
AU - Gojković, S.V.
AU - Kessler, M.
AU - Kalvoda, J.
AU - Pavlović, Vladimir D.
PY - 2007
UR - http://cer.ihtm.bg.ac.rs/handle/123456789/358
AB - 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.
PB - Pergamon-Elsevier Science Ltd, Oxford
T2 - Tetrahedron
T1 - Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound
VL - 63
IS - 40
SP - 9960
EP - 9969
DO - 10.1016/j.tet.2007.07.056
ER -
@article{
author = "Bjelaković, Mira and Krstić, Natalija and Juranić, Nenad and Dabović, Milan and Gojković, S.V. and Kessler, M. and Kalvoda, J. and Pavlović, Vladimir D.",
year = "2007",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/358",
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.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound",
volume = "63",
number = "40",
pages = "9960-9969",
doi = "10.1016/j.tet.2007.07.056"
}
Bjelaković M, Krstić N, Juranić N, Dabović M, Gojković S, Kessler M, Kalvoda J, Pavlović VD. Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound. Tetrahedron. 2007;63(40):9960-9969
Bjelaković, M., Krstić, N., Juranić, N., Dabović, M., Gojković, S.V., Kessler, M., Kalvoda, J.,& Pavlović, V. D. (2007). Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound.
TetrahedronPergamon-Elsevier Science Ltd, Oxford., 63(40), 9960-9969.
https://doi.org/10.1016/j.tet.2007.07.056
Bjelaković Mira, Krstić Natalija, Juranić Nenad, Dabović Milan, Gojković S.V., Kessler M., Kalvoda J., Pavlović Vladimir D., "Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound" 63, no. 40 (2007):9960-9969,
https://doi.org/10.1016/j.tet.2007.07.056 .
