Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound
Authorized Users Only
2007
Authors
Bjelaković, MiraKrstić, Natalija
Juranić, Nenad
Dabović, Milan
Gojković, S.V.
Kessler, M.
Kalvoda, J.
Pavlović, Vladimir D.
Article (Published version)
Metadata
Show full item recordAbstract
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:
18-Cyanopregnenolone acetate / 18-Phe,19-Gly-containing steroidal compound / 2D NMR analysis / STAP conceptSource:
Tetrahedron, 2007, 63, 40, 9960-9969Publisher:
- Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
DOI: 10.1016/j.tet.2007.07.056
ISSN: 0040-4020
WoS: 000252092100005
Scopus: 2-s2.0-34547982305
Collections
Institution/Community
IHTMTY - 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 - https://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 - Oxford : Pergamon-Elsevier Science Ltd 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", 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 = "Oxford : Pergamon-Elsevier Science Ltd", 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.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. in Tetrahedron Oxford : Pergamon-Elsevier Science Ltd., 63(40), 9960-9969. https://doi.org/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. in Tetrahedron. 2007;63(40):9960-9969. doi: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" in Tetrahedron, 63, no. 40 (2007):9960-9969, https://doi.org/10.1016/j.tet.2007.07.056 . .