Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
pH-Dependent Mutarotation of 1-Thioaldoses in Water. Unexpected Behavior of (2S)-D-Aldopyranoses
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Physical Chemistry.ORCID iD: 0000-0003-2673-075X
Show others and affiliations
2010 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, no 18, 6115-6121 p.Article in journal (Refereed) Published
Abstract [en]

The pH-dependent mutarotation of 1-thioaldopyranoses in aqueous media has been investigated. Anomerization readily occurred at lower and neutral pH for all aldopyranoses studied, whereas mainly for (2S)-D-aldopyranoses at higher pH. 1-Thio-D-mannopyranose and 1-thio-D-altropyranose showed very strong pH dependence where the anomeric equilibrium ratios changed dramatically from a preference for the beta-anomer at lower pH to the alpha-anomer at higher pH.

Place, publisher, year, edition, pages
2010. Vol. 75, no 18, 6115-6121 p.
Keyword [en]
Anomeric equilibrium, Anomerization, Aqueous media, Mannopyranose, Mutarotation, Neutral pH, PH dependence, PH-dependent
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-26704DOI: 10.1021/jo100826eISI: 000281585600007Scopus ID: 2-s2.0-77956498793OAI: oai:DiVA.org:kth-26704DiVA: diva2:372808
Note
QC 20101129 Uppdaterad från manuskript till artikel (20101129).Available from: 2010-11-29 Created: 2010-11-26 Last updated: 2017-12-12Bibliographically approved
In thesis
1. Dynamic Sulfur Chemistry: Screening, Evaluation and Catalysis
Open this publication in new window or tab >>Dynamic Sulfur Chemistry: Screening, Evaluation and Catalysis
2010 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis deals with the design, formation and evaluation of dynamic systems constructed by means of sulfur-containing reversible reactions, in organic and aqueous media and under mild conditions.

In a first part, the synthesis of thioglycoside derivatives, constituting the biologically relevant starting components of the dynamic systems, is described. In addition, the pD-profile of the mutarotation process in aqueous media for a series of 1-thioaldoses is reported and revealed an astonishing beta-anomeric preference for all the carbohydrate analogs under acidic or neutral conditions.

In a second part, the phosphine-catalyzed or -mediated disulfide metathesis for dynamic system generation in organic or aqueous media is presented, respectively. The direct in situ 1H STD-NMR resolution of a dynamic carbohydrate system in the presence of a target protein (Concanavalin A) proved the suitability and compatibility of such disulfide metathesis protocols for the discovery of biologically relevant ligands.

In a third part, hemithioacetal formation is demonstrated as a new and efficient reversible reaction for the spontaneous generation of a dynamic system, despite a virtual character of the component associations in basic aqueous media. The direct in situ 1H STD-NMR identification of the best dynamic beta-galactosidase inhibitors from the dynamic HTA system was performed and the results were confirmed by inhibition studies. Thus, the HTA product formed from the reaction between 1-thiogalactopyranose and a pyridine carboxaldehyde derivative provided the best dynamic inhibitor.

In a fourth and final part, a dynamic drug design strategy, where the best inhibitors from the aforementioned dynamic HTA system were used as model for the design of non-dynamic (or “static”) beta-galactosidase inhibitors, is depicted. Inhibition studies disclosed potent leads among the set of ligands.

Place, publisher, year, edition, pages
Stockholm: KTH, 2010. 84 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2010:14
Keyword
Dynamic combinatorial chemistry; dynamic sulfur chemistry; thioglycoside; mutarotation; disulfide metathesis; hemithioacetal formation; 1H STD-NMR; inhibition; phosphine; Concanavalin A; beta-galactosidase; dynamic drug discovery.
National Category
Chemical Sciences Organic Chemistry Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-12414 (URN)978-91-7415-618-8 (ISBN)
Public defence
2010-05-12, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
QC 20100621Available from: 2010-04-22 Created: 2010-04-20 Last updated: 2010-11-29Bibliographically approved
2. Photochemical Surface Functionalization: Synthesis, Nanochemistry and Glycobiological Studies
Open this publication in new window or tab >>Photochemical Surface Functionalization: Synthesis, Nanochemistry and Glycobiological Studies
2011 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis mainly deals with the development of photochemical approaches to immobilize carbohydrates on surfaces for glycobiological studies. These approaches have been incorporated into a number of state-of-the-art nanobio-platforms, including carbohydrate microarrays, surface plasmon resonance (SPR), quartz crystal microbalance (QCM), atomic force microscopy (AFM), and glyconanomaterials. All the surfaces have displayed good binding capabilities and selectivities after functionalization with carbohydrates, and a range of important data have been obtained concerning surface characteristics and carbohydrate-protein interactions, based on the platforms established. Besides, a variety of non-carbohydrate and carbohydrate-based molecules have been synthesized, during which process the mutarotation of 1-glycosyl thiols and the stereocontrol in 1-S-glycosylation reactions have been thoroughly studied.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2011. 86 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2011:47
Keyword
Carbohydrates, Glycobiology, Carbohydrate-protein interactions, Perfluorophenylazide (PFPA), Photochemistry, Carbohydrate surface immobilization, Carbohydrate microarrays, Surface plasmon resonance (SPR), Quartz crystal microbalance (QCM), Atomic force microscopy (AFM), Glyconanomaterials, Concanavalin A (Con A), Cyanovirin-N (CV-N), 1-Glycosyl thiols; Mutarotation, 1-S-glycosylation, Stereocontrol
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-41973 (URN)978-91-7501-072-4 (ISBN)
Public defence
2011-10-21, F3, Lindstedtsvägen 26, KTH, Stockholm, 13:00 (English)
Opponent
Supervisors
Note
QC 20111004Available from: 2011-10-04 Created: 2011-10-04 Last updated: 2011-10-04Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full textScopus

Authority records BETA

Brinck, Tore

Search in DiVA

By author/editor
Caraballo, RémiDeng, LingquanAmorim, LuisBrinck, ToreRamström, Olof
By organisation
Organic ChemistryPhysical Chemistry
In the same journal
Journal of Organic Chemistry
Chemical Sciences

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 87 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf