NDLI: Enantioselective Recognition of Aliphatic Amino Acids by β‐Cyclodextrin Derivatives Bearing Aromatic Organoselenium Moieties on the Primary or Secondary Side

Please wait, while we are loading the content...

Enantioselective Recognition of Aliphatic Amino Acids by β‐Cyclodextrin Derivatives Bearing Aromatic Organoselenium Moieties on the Primary or Secondary Side

Content Provider	Semantic Scholar
Author	You, Chang Cheng Zhang, Heng Yi Zhao, Yanli
Copyright Year	2003
Abstract	Spectrophotometric titrations have been performed in order to determine the stability constants of inclusion complexation of some aliphatic amino acids with four structurally related organoselenium-modified β-cyclodextrins: mono(6-phenylseleno-6-deoxy)-β-cyclodextrin (1a), mono[6-(p-methoxyphenylseleno)-6-deoxy]-β-cyclodextrin (1b), mono(2-phenylseleno-2-deoxy)-β-cyclodextrin (2a), and mono[2-(p-methoxyphenylseleno)-2-deoxy]-β-cyclodextrin (2b). Conformation analysis by circular dichroism and 2D NMR spectroscopic studies revealed that the aryl-substituted β-cyclodextrins gave self-inclusion intramolecular complexes in aqueous solution, while the extent of penetration depended both on the positions and on the structures of substituents. Quantitative investigation on the binding ability of the hosts with amino acids showed that they were able to recognize the size and the shape of guests, affording supramolecular complexes with quite small stability constants ranging from 24 to 355 M−1. The molecular recognition abilities are discussed from the viewpoints of induced-fitting mechanisms, geometric complementary, and cooperative binding processes. Furthermore, these β-cyclodextrin derivatives displayed considerable enantioselectivity towards L/D-amino acid isomers, giving the highest L-enantioselectivity (up to 8.4) for inclusion complexation between leucine and 2a. The binding modes of L/D-leucine with 1b were elucidated from NOESY studies and the chiral recognition phenomena were interpreted accordingly. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
Starting Page	1415
Ending Page	1422
Page Count	8
File Format	PDF HTM / HTML
DOI	10.1002/ejoc.200390199
Volume Number	2003
Alternate Webpage(s)	https://dr.ntu.edu.sg/bitstream/handle/10220/6950/2003-1415.pdf;jsessionid=78628DB645B014857BA7ECF429134DD1?sequence=1
Alternate Webpage(s)	https://doi.org/10.1002/ejoc.200390199
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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