13C Chemical Shift Tensors in Hypoxanthine and 6-Mercaptopurine
: Effects of Substitution, Tautomerism, and Intermolecular
Interactions

J 2010

13C Chemical Shift Tensors in Hypoxanthine and 6-Mercaptopurine : Effects of Substitution, Tautomerism, and Intermolecular Interactions

MALIŇÁKOVÁ, Kateřina; Lucie NOVOSADOVÁ; Manu LAHTINEN; Erkki KOLEHMAINEN; Jiří BRUS et al.

Základní údaje

Originální název

13C Chemical Shift Tensors in Hypoxanthine and 6-Mercaptopurine : Effects of Substitution, Tautomerism, and Intermolecular Interactions

Název česky

13C tenzory chemického posunu u hypoxanthinu a 6-merkaptopurinu : Vliv substituce, tautomerie a mezimolekulárních interakcí

Autoři

MALIŇÁKOVÁ, Kateřina ; Lucie NOVOSADOVÁ; Manu LAHTINEN; Erkki KOLEHMAINEN; Jiří BRUS a Radek MAREK

Vydání

The Journal of Physical Chemistry A, Washington, Americal Chemical Society, 2010, 1089-5639

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10403 Physical chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

DOI: 10.1021/jp9100619

Impakt faktor

Impact factor: 2.732

Kód RIV

RIV/00216224:14310/10:00042954

Organizační jednotka

Přírodovědecká fakulta

DOI

https://doi.org/10.1021/jp9100619

UT WoS

000273948100048

Klíčová slova anglicky

solid-state NMR; DFTcalculations; X-ray powder diffraction; hydrogen bonding; stacking interactions

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 20. 6. 2013 19:35, prof. RNDr. Radek Marek, Ph.D.

Anotace

ORIG CZ

V originále

Principal values of the 13C chemical shift tensor (CST) are measured for two biologically interesting and structurally related compounds, hypoxanthine and 6-mercaptopurine, and differences in the values are discussed with an attempt to reveal chemical shifts sensitive to substitution and prototropic tautomerism in the purine ring. Furthermore, methods of density-functional theory (DFT) are used to calculate principal values of the 13C chemical shift tensor and orientations of the principal components. Values calculated for isolated molecules are compared to those for several supramolecular clusters and then to experimental data to investigate the degree of modulation of the 13C CSTs by molecular packing. Focusing on the protonated carbons, C2 and C8, which are crucial for relaxation measurements, we show that neglecting intermolecular interactions can lead to errors as large as 30 ppm in the delta22 principal component.

Česky

Hodnoty hlavních složek 13C NMR tenzoru chemického posunu jsou měřeny pro dvě biologicky zajímavé a strukturně podobné sloučeniny, hypoxanthin and 6-mercaptopurin. Rozdíly v hodnotách jsou diskutovány z pohledu substituce a tautomerie.

Návaznosti

LC06030, projekt VaV

Název: Biomolekulární centrum

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Biomolekulární centrum

MSM0021622413, záměr

Název: Proteiny v metabolismu a při interakci organismů s prostředím

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Proteiny v metabolismu a při interakci organismů s prostředím

Přiložené soubory

JPCA10_114_1985.pdf

Požádat o autorskou verzi souboru

Citovat

MALIŇÁKOVÁ, Kateřina; Lucie NOVOSADOVÁ; Manu LAHTINEN; Erkki KOLEHMAINEN; Jiří BRUS a Radek MAREK. 13C Chemical Shift Tensors in Hypoxanthine and 6-Mercaptopurine : Effects of Substitution, Tautomerism, and Intermolecular Interactions. The Journal of Physical Chemistry A. Washington: Americal Chemical Society, 2010, roč. 114, č. 4, s. 1985-1995. ISSN 1089-5639. Dostupné z: https://doi.org/10.1021/jp9100619.

@article{858923,
   author = {Maliňáková, Kateřina and Novosadová, Lucie and Lahtinen, Manu and Kolehmainen, Erkki and Brus, Jiří and Marek, Radek},
   article_location = {Washington},
   article_number = {4},
   doi = {https://doi.org/10.1021/jp9100619},
   keywords = {solid-state NMR; DFTcalculations; X-ray powder diffraction; hydrogen bonding; stacking interactions},
   language = {eng},
   issn = {1089-5639},
   journal = {The Journal of Physical Chemistry A},
   title = {13C Chemical Shift Tensors in Hypoxanthine and 6-Mercaptopurine : Effects of Substitution, Tautomerism, and Intermolecular Interactions},
   url = {http://dx.doi.org/10.1021/jp9100619},
   volume = {114},
   year = {2010}
}

TY  - JOUR
ID  - 858923
AU  - Maliňáková, Kateřina - Novosadová, Lucie - Lahtinen, Manu - Kolehmainen, Erkki - Brus, Jiří - Marek, Radek
PY  - 2010
TI  - 13C Chemical Shift Tensors in Hypoxanthine and 6-Mercaptopurine : Effects of Substitution, Tautomerism, and Intermolecular Interactions
JF  - The Journal of Physical Chemistry A
VL  - 114
IS  - 4
SP  - 1985-1995
EP  - 1985-1995
PB  - Americal Chemical Society
SN  - 10895639
KW  - solid-state NMR
KW  - DFTcalculations
KW  - X-ray powder diffraction
KW  - hydrogen bonding
KW  - stacking interactions
UR  - http://dx.doi.org/10.1021/jp9100619
L2  - http://dx.doi.org/10.1021/jp9100619
N2  - Principal values of the 13C chemical shift tensor (CST) are measured for two biologically interesting and structurally related compounds, hypoxanthine and 6-mercaptopurine, and differences in the values are discussed with an attempt to reveal chemical shifts sensitive to substitution and prototropic tautomerism in the purine ring. Furthermore, methods of density-functional theory (DFT) are used to calculate principal values of the 13C chemical shift tensor and orientations of the principal components. Values calculated for isolated molecules are compared to those for several supramolecular clusters and then to experimental data to investigate the degree of modulation of the 13C CSTs by molecular packing. Focusing on the protonated carbons, C2 and C8, which are crucial for relaxation measurements, we show that neglecting intermolecular interactions can lead to errors as large as 30 ppm in the delta22 principal component.
ER  -

MALIŇÁKOVÁ, Kateřina; Lucie NOVOSADOVÁ; Manu LAHTINEN; Erkki KOLEHMAINEN; Jiří BRUS a Radek MAREK. 13C Chemical Shift Tensors in Hypoxanthine and 6-Mercaptopurine : Effects of Substitution, Tautomerism, and Intermolecular Interactions. \textit{The Journal of Physical Chemistry A}. Washington: Americal Chemical Society, 2010, roč.~114, č.~4, s.~1985-1995. ISSN~1089-5639. Dostupné z: https://doi.org/10.1021/jp9100619.

Přehled o publikaci