Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound
Samo za registrovane korisnike
2007
Autori
Bjelaković, MiraKrstić, Natalija
Juranić, Nenad
Dabović, Milan
Gojković, S.V.
Kessler, M.
Kalvoda, J.
Pavlović, Vladimir D.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
18-Cyanopregnenolone acetate / 18-Phe,19-Gly-containing steroidal compound / 2D NMR analysis / STAP conceptIzvor:
Tetrahedron, 2007, 63, 40, 9960-9969Izdavač:
- Oxford : Pergamon-Elsevier Science Ltd
Finansiranje / projekti:
- Sinteza različitih korisnih proizvoda iz steroidnih molekula (RS-MESTD-MPN2006-2010-142033)
DOI: 10.1016/j.tet.2007.07.056
ISSN: 0040-4020
WoS: 000252092100005
Scopus: 2-s2.0-34547982305
Institucija/grupa
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 . .