Enantioselective recognition of aliphatic amino acids by β-cyclodextrin derivatives bearing aromatic organoselenium moieties on the primary or secondary side
Spectrophotometric titrations have been performed in order to determine the stability constants of inclusion complexation of some aliphatic amino acids with four structurally...
| Autors principals: | , , , |
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| Altres autors: | |
| Format: | Journal Article |
| Publicat: |
2011
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| Matèries: | |
| Accés en línia: | https://hdl.handle.net/10356/92240 http://hdl.handle.net/10220/6950 |
| _version_ | 1826123603335184384 |
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| author | Liu, Yu You, Chang Cheng Zhang, Heng Yi Zhao, Yanli |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Liu, Yu You, Chang Cheng Zhang, Heng Yi Zhao, Yanli |
| author_sort | Liu, Yu |
| collection | NTU |
| description | 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. |
| first_indexed | 2024-10-01T06:07:02Z |
| format | Journal Article |
| id | ntu-10356/92240 |
| institution | Nanyang Technological University |
| last_indexed | 2024-10-01T06:07:02Z |
| publishDate | 2011 |
| record_format | dspace |
| spelling | ntu-10356/922402023-02-28T19:34:16Z Enantioselective recognition of aliphatic amino acids by β-cyclodextrin derivatives bearing aromatic organoselenium moieties on the primary or secondary side Liu, Yu You, Chang Cheng Zhang, Heng Yi Zhao, Yanli School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry 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. Accepted version 2011-08-01T06:06:54Z 2019-12-06T18:19:51Z 2011-08-01T06:06:54Z 2019-12-06T18:19:51Z 2003 2003 Journal Article Liu, Y., You, C. C., Zhang, H. Y., & Zhao, Y. L. (2003). Enantioselective recognition of aliphatic amino acids by β-cyclodextrin derivatives bearing aromatic organoselenium moieties on the primary or secondary side. European Journal of Organic Chemistry, 2003(8), 1415-1422. https://hdl.handle.net/10356/92240 http://hdl.handle.net/10220/6950 10.1002/ejoc.200390199 159639 European journal of organic chemistry © 2003 Wiley-VCH Verlag. application/pdf |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry Liu, Yu You, Chang Cheng Zhang, Heng Yi Zhao, Yanli Enantioselective recognition of aliphatic amino acids by β-cyclodextrin derivatives bearing aromatic organoselenium moieties on the primary or secondary side |
| title | Enantioselective recognition of aliphatic amino acids by β-cyclodextrin derivatives bearing aromatic organoselenium moieties on the primary or secondary side |
| title_full | Enantioselective recognition of aliphatic amino acids by β-cyclodextrin derivatives bearing aromatic organoselenium moieties on the primary or secondary side |
| title_fullStr | Enantioselective recognition of aliphatic amino acids by β-cyclodextrin derivatives bearing aromatic organoselenium moieties on the primary or secondary side |
| title_full_unstemmed | Enantioselective recognition of aliphatic amino acids by β-cyclodextrin derivatives bearing aromatic organoselenium moieties on the primary or secondary side |
| title_short | Enantioselective recognition of aliphatic amino acids by β-cyclodextrin derivatives bearing aromatic organoselenium moieties on the primary or secondary side |
| title_sort | enantioselective recognition of aliphatic amino acids by β cyclodextrin derivatives bearing aromatic organoselenium moieties on the primary or secondary side |
| topic | DRNTU::Science::Chemistry::Organic chemistry |
| url | https://hdl.handle.net/10356/92240 http://hdl.handle.net/10220/6950 |
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