Enantiomeric recognition of amino acid ester salts by beta-cyclodextrin derivatives: an experimental and computational study
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F46747885%3A24620%2F16%3A00000641" target="_blank" >RIV/46747885:24620/16:00000641 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.3998/ark.5550190.p009.657" target="_blank" >http://dx.doi.org/10.3998/ark.5550190.p009.657</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3998/ark.5550190.p009.657" target="_blank" >10.3998/ark.5550190.p009.657</a>
Alternative languages
Result language
angličtina
Original language name
Enantiomeric recognition of amino acid ester salts by beta-cyclodextrin derivatives: an experimental and computational study
Original language description
beta-cyclodextrin derivatives bearing benzoyl (beta-CD-1) and naphthoyl beta-CD-2) moieties have been synthesized from salicylic acid and 3-hydroxy-2-naphthoic acid by a convenient method in 60% and 58% yields, respectively, and were tested for enantiomeric recognition of amino acid ester derivatives. Their ability to discriminate between various L-/D-amino acid methyl ester hydrochloride salts was examined using the H-1 NMR titration method in DMSO-d(6) at 25 degrees C. beta-CD- 2 produced a fairly good discrimination of tryptophan ester salts with a binding constant of 4041 M-1 for L-salt compared with 2864 M-1 for D-salt, which corresponds to a difference of 0.21 kcal mol(-1) in binding free energies. The binding free energies obtained from molecular dynamic calculation by MM/PB(GB) SA are consistent with those obtained from the experimental results.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Arkivoc
ISSN
1551-7012
e-ISSN
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Volume of the periodical
2016
Issue of the periodical within the volume
5
Country of publishing house
US - UNITED STATES
Number of pages
19
Pages from-to
249-267
UT code for WoS article
000385801100017
EID of the result in the Scopus database
2-s2.0-84991396117