Conformations and tautomers of tetracycline

Beitrag in einer Fachzeitschrift


Details zur Publikation

Autorinnen und Autoren: Othersen O, Beierlein F, Lanig H, Clark T
Zeitschrift: Journal of Physical Chemistry B
Verlag: American Chemical Society
Jahr der Veröffentlichung: 2003
Band: 107
Heftnummer: 49
Seitenbereich: 13743-13749
ISSN: 1520-6106
eISSN: 1520-5207


Abstract


Density functional theory (DFT) has been used to investigate the conformations and tautomeric forms of neutral tetracycline in aqueous solution. The results suggest that the extended conformation is 3-3.5 kcal mol(-1) more stable than the twisted one for equivalent tautomers and that as many as six different tautomeric forms lie within 10 kcal mol(-1) of the most stable one. The energetic preference for the extended conformation is a solvent effect. Calculated infrared, NMR, and UV/vis spectra are used to suggest ways of differentiating between tautomers. and conformations experimentally. It is shown that the (13)C chemical shifts of C4a, C5, and C6 can be used to distinguish between the twisted and extended conformations.



FAU-Autorinnen und Autoren / FAU-Herausgeberinnen und Herausgeber

Beierlein, Frank Dr.
Computer-Chemie-Centrum
Clark, Timothy apl. Prof. Dr.
Computer-Chemie-Centrum
Lanig, Harald PD Dr.
Exzellenz-Cluster Engineering of Advanced Materials


Zitierweisen

APA:
Othersen, O., Beierlein, F., Lanig, H., & Clark, T. (2003). Conformations and tautomers of tetracycline. Journal of Physical Chemistry B, 107(49), 13743-13749. https://dx.doi.org/10.1021/jp0364506

MLA:
Othersen, Olaf, et al. "Conformations and tautomers of tetracycline." Journal of Physical Chemistry B 107.49 (2003): 13743-13749.

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