About: Absolute Configuration of a Cyclic Dipeptide Reflected in Vibrational Optical Activity: Ab Initio and Experimental Investigation

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	The ability of Raman optical activity (ROA) and vibrational circular dichroism (VCD) experiments to determine the absolute configuration of chiral molecules with multiple stereogenic centers was explored for four diastereoisomers of a conformationally flexible cyclic dipeptide, cyclo(Arg-Tyr-(OMe)). The reliability of the interpretation depended on the correct description of the molecular conformation, which was found to be strongly affected by intramolecular interactions. In particular, when dispersion corrections were included in the density functional theory calculations, the simulated spectra matched the experimental observations well. Experimental and theoretical ROA and VCD spectra were well correlated for all the absolute configurations (RS, SR, SS, and RR) of protonated cyclo(Arg-Tyr(OMe)). These spectroscopies thus appear useful not only for reliable determination of the absolute configuration and conformation but also in revealing the role of hydrogen bonds and C-R center dot center dot center dot pi interactions in the structure stabilization, which can potentially be used when designing enzyme inhibitors and supramolecular architectures. The ability of Raman optical activity (ROA) and vibrational circular dichroism (VCD) experiments to determine the absolute configuration of chiral molecules with multiple stereogenic centers was explored for four diastereoisomers of a conformationally flexible cyclic dipeptide, cyclo(Arg-Tyr-(OMe)). The reliability of the interpretation depended on the correct description of the molecular conformation, which was found to be strongly affected by intramolecular interactions. In particular, when dispersion corrections were included in the density functional theory calculations, the simulated spectra matched the experimental observations well. Experimental and theoretical ROA and VCD spectra were well correlated for all the absolute configurations (RS, SR, SS, and RR) of protonated cyclo(Arg-Tyr(OMe)). These spectroscopies thus appear useful not only for reliable determination of the absolute configuration and conformation but also in revealing the role of hydrogen bonds and C-R center dot center dot center dot pi interactions in the structure stabilization, which can potentially be used when designing enzyme inhibitors and supramolecular architectures. (en)
Title	Absolute Configuration of a Cyclic Dipeptide Reflected in Vibrational Optical Activity: Ab Initio and Experimental Investigation Absolute Configuration of a Cyclic Dipeptide Reflected in Vibrational Optical Activity: Ab Initio and Experimental Investigation (en)
skos:prefLabel	Absolute Configuration of a Cyclic Dipeptide Reflected in Vibrational Optical Activity: Ab Initio and Experimental Investigation Absolute Configuration of a Cyclic Dipeptide Reflected in Vibrational Optical Activity: Ab Initio and Experimental Investigation (en)
skos:notation	RIV/61388963:_____/12:00377378!RIV13-AV0-61388963
http://linked.open...avai/predkladatel	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(GAP208/11/0105), P(LH11033), Z(AV0Z40550506)
http://linked.open...iv/cisloPeriodika	10
http://linked.open...vai/riv/dodaniDat	2013
http://linked.open...aciTvurceVysledku	Bouř, Petr Hudecová, Jana
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Ústav organické chemie a biochemie AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	120791
http://linked.open...ai/riv/idVysledku	RIV/61388963:_____/12:00377378
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	cyclic dipeptide; vibrational otpical activity; density functional theory; dispersion; electronic circular dichroism (en)
http://linked.open.../riv/klicoveSlovo	cyclic dipeptide electronic circular dichroism vibrational otpical activity density functional theory dispersion
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[4693CE4C1F38]
http://linked.open...i/riv/nazevZdroje	Journal of Physical Chemistry A
http://linked.open...in/vavai/riv/obor	CF
http://linked.open...ichTvurcuVysledku	2 (xsd:int)
http://linked.open...cetTvurcuVysledku	9 (xsd:int)
http://linked.open...vavai/riv/projekt	Expanding the Optical Activity Method to the Realm of Biomolecules Development of spectroscopic methods for structural studies of biomolecules
http://linked.open...UplatneniVysledku	2012
http://linked.open...v/svazekPeriodika	116
http://linked.open...iv/tvurceVysledku	Bouř, Petr Li, X. Novotná, J. Urbanová, M. Hopmann, K. H. Ruud, K. Hudecová, Jana Stensen, W. Svendsen, J. S.
http://linked.open...ain/vavai/riv/wos	000301509400019
http://linked.open...n/vavai/riv/zamer	Regulace biologických procesů: Chemické modulátory vybraných systémů významných pro medicínu a zemědělství
issn	1089-5639
number of pages	10 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/jp211454v
is http://linked.open...avai/riv/vysledek of	Absolute Configuration of a Cyclic Dipeptide Reflected in Vibrational Optical Activity: Ab Initio and Experimental Investigation

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