NDLI: Chiral recognition of abacavir enantiomers by (2-hydroxy)propyl-β-cyclodextrin: UHPLC, NMR and DFT studies

Content Provider	Springer Nature Link
Author	Reyes Reyes, M. L. Roa Morales, Gabriela Melgar Fernández, Roberto Reyes Pérez, Horacio Gómez Oliván, Leobardo M. Gonzalez Rivas, Nelly Bautista Renedo, Joanatan Balderas Hernández, Patricia
Copyright Year	2015
Abstract	The diastereomeric complexation of both abacavir (ABA) and its enantiomer (ABAE) with (2-hydroxy)propyl-β-cyclodextrin (2HPβCD) with a degree of substitution of seven was studied. The apparent binding constants of diasteromeric complexes, ABA-2HPβCD and ABAE-2HPβCD were determined by ultra high-pressure liquid chromatography (UHPLC) and found to be 517.0 and 684.4 M$^{−1}$ respectively. The stoichiometry of the complexes was determined by UHPLC and by the continuous variation method using nuclear magnetic resonance spectroscopy giving 1:1 complexes. The apparent binding constants decrease as the temperatures increases. The observed enantio-differentiation was analyzed theoretically by density functional theory at the PBE/6-31 g** level using a polarizable continuous model (PCM) for solvent effects, the most stable complexes are the ones in which the chiral cyclopentenyl moiety is included in the cavity of CD and the protonated purine ring interact with the hydroxypropyl groups of 2HPβCD. The differences in stability of diasteromeric complexes, due to different intermolecular interactions are consistent with experimental data, providing further insights in the formation of inclusion complexes.
Starting Page	373
Ending Page	382
Page Count	10
File Format	PDF
ISSN	13883127
Journal	Journal of Inclusion Phenomena and Macrocyclic Chemistry
Volume Number	82
Issue Number	3-4
e-ISSN	15731111
Language	English
Publisher	Springer Netherlands
Publisher Date	2015-03-21
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Terachem Diasteromeric complexes Cyclodextrins Inclusion complex Density functional theory Solvent effects Organic Chemistry Food Science Crystallography
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics Food Science

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in

NMR spectroscopic characterization of inclusion complexes of hydroxy-substituted naphthalenes with native and modified β-cyclodextrins

Inclusion complexes of lamotrigine and hydroxy propyl β-cyclodextrin: solid state characterization and dissolution studies

NMR Investigations of Inclusion Complexes between β-Cyclodextrin and Naphthalene/Anthraquinone Derivatives

Preparation and characterization of β-sitosterol/β-cyclodextrin crystalline inclusion complexes

$^{1}$H and $^{13}$C NMR investigations of inclusion complexes between β-cyclodextrin and naphthalenediamines/phenol derivatives

Complex formation of fenchone with α-cyclodextrin: NMR titrations

Comparison between 2-hydroxypropyl-β-cyclodextrin and 2-hydroxypropyl-γ-cyclodextrin for inclusion complex formation with danazol

Synthesis and inclusion properties study of some mono 6-amino β-cyclodextrin dimers bridged by N,N-succinyldiamide linkers

Inclusion complexes of 2-phenoxyethanol and alkoxyethanols in cyclodextrins: an $^{1}$H NMR study

Chiral recognition of abacavir enantiomers by (2-hydroxy)propyl-β-cyclodextrin: UHPLC, NMR and DFT studies

Similar Documents

NMR spectroscopic characterization of inclusion complexes of hydroxy-substituted naphthalenes with native and modified β-cyclodextrins

Inclusion complexes of lamotrigine and hydroxy propyl β-cyclodextrin: solid state characterization and dissolution studies

NMR Investigations of Inclusion Complexes between β-Cyclodextrin and Naphthalene/Anthraquinone Derivatives

Preparation and characterization of β-sitosterol/β-cyclodextrin crystalline inclusion complexes

$^{1}$H and $^{13}$C NMR investigations of inclusion complexes between β-cyclodextrin and naphthalenediamines/phenol derivatives

Complex formation of fenchone with α-cyclodextrin: NMR titrations

Comparison between 2-hydroxypropyl-β-cyclodextrin and 2-hydroxypropyl-γ-cyclodextrin for inclusion complex formation with danazol

Synthesis and inclusion properties study of some mono 6-amino β-cyclodextrin dimers bridged by N,N-succinyldiamide linkers

Inclusion complexes of 2-phenoxyethanol and alkoxyethanols in cyclodextrins: an $^{1}$H NMR study

Chiral recognition of abacavir enantiomers by (2-hydroxy)propyl-β-cyclodextrin: UHPLC, NMR and DFT studies