title: Trimodal Control of Ion-Transport Activity on Cyclo-oligo-(1→6)-β-D-glucosamine-Based Artificial Ion-Transport Systems.
abstract: Cyclo-oligo-(1→6)-β-D-glucosamines functionalized with hydrophobic tails are reported as a new class of transmembrane ion-transport system. These macrocycles with hydrophilic cavities were introduced as an alternative to cyclodextrins, which are supramolecular systems with hydrophobic cavities. The transport activities of these glycoconjugates were manipulated by altering the oligomericity of the macrocycles, as well as the length and number of attached tails. Hydrophobic tails of 3 different sizes were synthesized and coupled with each glucosamine scaffold through the amide linkage to obtain 18 derivatives. The ion-transport activity increased from di- to tetrameric glucosamine macrocycles, but decreased further when flexible pentameric glucosamine was introduced. The ion-transport activity also increased with increasing length of attached linkers. For a fixed length of linkers, the transport activity decreased when the number of such tails was reduced. All glycoconjugates displayed a uniform anion-selectivity sequence: Cl(-) >Br(-) >I(-) . From theoretical studies, hydrogen bonding between the macrocycle backbone and the anion bridged through water molecules was observed.
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Pune, Dr. Homi Bhabha Road, Pashan, Pune 411008, Maharashtra (India), Fax: (+91) 20-25899790.
authors.forename: Arundhati
authors.initials: A
authors.lastname: Roy
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Pune, Dr. Homi Bhabha Road, Pashan, Pune 411008, Maharashtra (India), Fax: (+91) 20-25899790.
authors.forename: Tanmoy
authors.initials: T
authors.lastname: Saha
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow (Russia), Fax: (+7) 499-1358784.
authors.forename: Marina L
authors.initials: ML
authors.lastname: Gening
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow (Russia), Fax: (+7) 499-1358784.
authors.forename: Denis V
authors.initials: DV
authors.lastname: Titov
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow (Russia), Fax: (+7) 499-1358784.
authors.forename: Alexey G
authors.initials: AG
authors.lastname: Gerbst
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow (Russia), Fax: (+7) 499-1358784.
authors.forename: Yury E
authors.initials: YE
authors.lastname: Tsvetkov
authors.affiliation: Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prospect 47, 119991 Moscow (Russia), Fax: (+7) 499-1358784. nen@ioc.ac.ru.
authors.forename: Nikolay E
authors.initials: NE
authors.lastname: Nifantiev
authors.affiliation: Department of Chemistry, Indian Institute of Science Education and Research Pune, Dr. Homi Bhabha Road, Pashan, Pune 411008, Maharashtra (India), Fax: (+91) 20-25899790. ptalukdar@iiserpune.ac.in.
authors.forename: Pinaki
authors.initials: P
authors.lastname: Talukdar
mesh_terms: D000227:Adenine Nucleotides; D000838:Anions / Q000737:chemistry; D005944:Glucosamine / Q000031:analogs & derivatives / Q000737:chemistry*; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D017136:Ion Transport; D009841:Oligonucleotides; D009843:Oligoribonucleotides
chemical_list: D000227:Adenine Nucleotides; D000838:Anions; D009841:Oligonucleotides; D009843:Oligoribonucleotides; C023505:2',5'-oligoadenylate; D005944:Glucosamine
keywords: anions; glycoconjugates; ion channels; macrocycles; structure-activity relationships