The conformation of biliverdin in dimethyl sulfoxide: implications for the coordination with copper
Само за регистроване кориснике
2019
Аутори
Dimitrijević, Milena
Žižić, Milan

Piccioli, Mario

Bogdanović Pristov, Jelena

Spasojević, Ivan

Чланак у часопису (Објављена верзија)

Метаподаци
Приказ свих података о документуАпстракт
Biliverdin (BV) structure was analyzed by using NMR techniques and unrestricted density function theory simulations to explain the incapacity of BV to build coordination complex(es) with Cu2+ in dimethyl sulfoxide, which was confirmed by UV-Vis, EPR and NMR spectroscopy. NMR showed that N atoms are protonated in all four pyrrole rings. The structure is stabilized by two hydrogen bonds between NH moieties and carbonyl oxygens from opposite terminal pyrrole rings, and by the bending of propionyl chain with carboxyl group out of the plain toward central position of BV. The simulations of deprotonated BV, which builds copper complexes in water and chloroform as described previously, showed a different conformation and organization of hydrogen bonds. Taking into account that deprotonation represents a critical step in coordinate bonds formation, the protonation of an additional N atom may represent a key difference between the interactions of BV with copper in different solvents.
Кључне речи:
UDFT / NOESY / Hydrogen bonds / Copper / BiliverdinИзвор:
Structural Chemistry, 2019, 30, 6, 2159-2166Издавач:
- Springer/Plenum Publishers, New York
DOI: 10.1007/s11224-019-01354-5
ISSN: 1040-0400
WoS: 000494698700010
Scopus: 2-s2.0-85066063987
Институција/група
Institut za multidisciplinarna istraživanjaTY - JOUR AU - Dimitrijević, Milena AU - Žižić, Milan AU - Piccioli, Mario AU - Bogdanović Pristov, Jelena AU - Spasojević, Ivan PY - 2019 UR - http://rimsi.imsi.bg.ac.rs/handle/123456789/1210 AB - Biliverdin (BV) structure was analyzed by using NMR techniques and unrestricted density function theory simulations to explain the incapacity of BV to build coordination complex(es) with Cu2+ in dimethyl sulfoxide, which was confirmed by UV-Vis, EPR and NMR spectroscopy. NMR showed that N atoms are protonated in all four pyrrole rings. The structure is stabilized by two hydrogen bonds between NH moieties and carbonyl oxygens from opposite terminal pyrrole rings, and by the bending of propionyl chain with carboxyl group out of the plain toward central position of BV. The simulations of deprotonated BV, which builds copper complexes in water and chloroform as described previously, showed a different conformation and organization of hydrogen bonds. Taking into account that deprotonation represents a critical step in coordinate bonds formation, the protonation of an additional N atom may represent a key difference between the interactions of BV with copper in different solvents. PB - Springer/Plenum Publishers, New York T2 - Structural Chemistry T1 - The conformation of biliverdin in dimethyl sulfoxide: implications for the coordination with copper EP - 2166 IS - 6 SP - 2159 VL - 30 DO - 10.1007/s11224-019-01354-5 ER -
@article{ author = "Dimitrijević, Milena and Žižić, Milan and Piccioli, Mario and Bogdanović Pristov, Jelena and Spasojević, Ivan", year = "2019", abstract = "Biliverdin (BV) structure was analyzed by using NMR techniques and unrestricted density function theory simulations to explain the incapacity of BV to build coordination complex(es) with Cu2+ in dimethyl sulfoxide, which was confirmed by UV-Vis, EPR and NMR spectroscopy. NMR showed that N atoms are protonated in all four pyrrole rings. The structure is stabilized by two hydrogen bonds between NH moieties and carbonyl oxygens from opposite terminal pyrrole rings, and by the bending of propionyl chain with carboxyl group out of the plain toward central position of BV. The simulations of deprotonated BV, which builds copper complexes in water and chloroform as described previously, showed a different conformation and organization of hydrogen bonds. Taking into account that deprotonation represents a critical step in coordinate bonds formation, the protonation of an additional N atom may represent a key difference between the interactions of BV with copper in different solvents.", publisher = "Springer/Plenum Publishers, New York", journal = "Structural Chemistry", title = "The conformation of biliverdin in dimethyl sulfoxide: implications for the coordination with copper", pages = "2166-2159", number = "6", volume = "30", doi = "10.1007/s11224-019-01354-5" }
Dimitrijević, M., Žižić, M., Piccioli, M., Bogdanović Pristov, J.,& Spasojević, I.. (2019). The conformation of biliverdin in dimethyl sulfoxide: implications for the coordination with copper. in Structural Chemistry Springer/Plenum Publishers, New York., 30(6), 2159-2166. https://doi.org/10.1007/s11224-019-01354-5
Dimitrijević M, Žižić M, Piccioli M, Bogdanović Pristov J, Spasojević I. The conformation of biliverdin in dimethyl sulfoxide: implications for the coordination with copper. in Structural Chemistry. 2019;30(6):2159-2166. doi:10.1007/s11224-019-01354-5 .
Dimitrijević, Milena, Žižić, Milan, Piccioli, Mario, Bogdanović Pristov, Jelena, Spasojević, Ivan, "The conformation of biliverdin in dimethyl sulfoxide: implications for the coordination with copper" in Structural Chemistry, 30, no. 6 (2019):2159-2166, https://doi.org/10.1007/s11224-019-01354-5 . .