Folding of a beta-cyclodextrin monosubstituted at its secondary face, revealed by NMR studies of local structural variations

Authors
Berthault, P Birlirakis, N
Citation
P. Berthault et N. Birlirakis, Folding of a beta-cyclodextrin monosubstituted at its secondary face, revealed by NMR studies of local structural variations, TETRAHEDR-A, 11(12), 2000, pp. 2463-2469
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
12
Year of publication
2000
Pages
2463 - 2469
Database
ISI
SICI code
0957-4166(20000630)11:12<2463:FOABMA>2.0.ZU;2-M
Abstract
The H-1 NMR study of a CD mono-functionalized at its secondary face is pres ented. It is shown that mono-(3-Tyr-3-deoxy-altro)-beta-CD undergoes a solv ent-dependent conformational change. Passing from organic medium to water, a stable self-inclusion complex is formed. Such a folding is accompanied by a local structural modification of the substituted altrose ring, which can be easily detected from the important variation of its H1-H2 coupling cons tant. (C) 2000 Elsevier Science Ltd. All rights reserved.