Rigid duplex alpha-cyclodextrin reversibly connected with disulfide bonds. Synthesis and inclusion complexes

The Journal of Organic Chemistry
Lukáš KumprechtTomás Kraus

Abstract

The rigid duplex cyclodextrin 6 composed of two alpha-cyclodextrin macrocycles connected with two disulfide bonds in "transannular" (C6(I), C6(IV)) positions was prepared from partially debenzylated alpha-cyclodextrin 1 in four steps in 73% overall yield. In the last key step involving oxidative coupling of the thiol 5, predominance of the target duplex 6 can be attained under conditions of thermodynamic control. The structure of duplex cyclodextrin was established by MS as well as 2-D NMR methods and confirmed by a single-crystal X-ray analysis. The ability of the duplex cyclodextrin 6 to bind alpha,omega-alkanediols (C9-C14) and 1-alkanols (C9 and C10) was studied by isothermal titration calorimetry in aqueous solutions. The stability constants of the complexes gradually increase with the alkyl chain length and reach an unprecedently high value of K = 8.6 x 10(9) M(-1) for 1,14-tetradecanediol. It was found that the doubly bridged dimer 6 exhibits higher binding affinity toward the series of alpha,omega-alkanediols than the singly bridged analogue 10 by about 2 orders of magnitude in K (M(-1)) or 3.1-3.3 kcal/mol in deltaG(o), the enhancement being due to enthalpic factors. Theoretical calculations using DFT-D methods suggest...Continue Reading

References

Feb 19, 2002·Chemical Reviews·Mikhail V. Rekharsky, Yoshihisa Inoue
Aug 5, 1997·Chemical Reviews·Kenneth A. Connors
Nov 18, 2003·Angewandte Chemie·Alessandro ScarsoJulius Rebek
Jan 30, 2004·Journal of the American Chemical Society·W Bruce TurnbullSteve W Homans
Oct 14, 2004·Journal of the American Chemical Society·Alessandro ScarsoJulius Rebek
Feb 1, 2005·Journal of Natural Products·Guido F PauliDavid C Lankin
Jun 17, 2005·Organic Letters·Kevin R WestSijbren Otto
Jul 21, 2006·The Journal of Physical Chemistry. B·Joel Tellinghuisen
Sep 14, 2006·Chemical Reviews·Peter T CorbettSijbren Otto
Dec 29, 2006·Chemistry & Biodiversity·Olivia BistriPierre Sinaÿ
Jul 27, 2007·Chemistry : a European Journal·Olivia BistriMatthieu Sollogoub

❮ Previous
Next ❯

Citations

Apr 13, 2013·Chemical Reviews·Min Hee LeeJong Seung Kim
Mar 18, 2010·Chemical Communications : Chem Comm·Thomas LecourtMatthieu Sollogoub
Apr 11, 2015·Organic & Biomolecular Chemistry·Yara Ruiz GarcíaAnnemieke Madder
Jan 24, 2015·Organic & Biomolecular Chemistry·Sergey VolkovTomáš Kraus
Nov 26, 2014·Physical Chemistry Chemical Physics : PCCP·Rares StiufiucConstantin M Lucaciu
May 29, 2010·Organic & Biomolecular Chemistry·Olivia Bistri-AslanoffMatthieu Sollogoub
Nov 3, 2010·Chirality·Petr MaloňVladimír Baumruk
Jun 3, 2015·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Marianna Gregova TrencanovaDusan Velic
Apr 26, 2019·Beilstein Journal of Organic Chemistry·Iveta Chena TicháJindřich Jindřich
Sep 1, 2011·Organic & Biomolecular Chemistry·Viktor MojrTomáš Kraus
Dec 16, 2010·Journal of Molecular Recognition : JMR·Robert J Falconer, Brett M Collins
Jun 15, 2011·Organic Letters·Aixia WangChang-Chun Ling
Aug 28, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Petr Kasal, Jindřich Jindřich

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.