Endre søk
RefereraExporteraLink to record
Permanent link

Direct link
Referera
Referensformat
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annet format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annet språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf
pH-Dependent Mutarotation of 1-Thioaldoses in Water. Unexpected Behavior of (2S)-D-Aldopyranoses
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Fysikalisk kemi.ORCID-id: 0000-0003-2673-075X
Vise andre og tillknytning
2010 (engelsk)Inngår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 75, nr 18, s. 6115-6121Artikkel i tidsskrift (Fagfellevurdert) 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.

sted, utgiver, år, opplag, sider
2010. Vol. 75, nr 18, s. 6115-6121
Emneord [en]
Anomeric equilibrium, Anomerization, Aqueous media, Mannopyranose, Mutarotation, Neutral pH, PH dependence, PH-dependent
HSV kategori
Identifikatorer
URN: urn:nbn:se:kth:diva-26704DOI: 10.1021/jo100826eISI: 000281585600007Scopus ID: 2-s2.0-77956498793OAI: oai:DiVA.org:kth-26704DiVA, id: diva2:372808
Merknad
QC 20101129 Uppdaterad från manuskript till artikel (20101129).Tilgjengelig fra: 2010-11-29 Laget: 2010-11-26 Sist oppdatert: 2017-12-12bibliografisk kontrollert
Inngår i avhandling
1. Dynamic Sulfur Chemistry: Screening, Evaluation and Catalysis
Åpne denne publikasjonen i ny fane eller vindu >>Dynamic Sulfur Chemistry: Screening, Evaluation and Catalysis
2010 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Stockholm: KTH, 2010. s. 84
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2010:14
Emneord
Dynamic combinatorial chemistry; dynamic sulfur chemistry; thioglycoside; mutarotation; disulfide metathesis; hemithioacetal formation; 1H STD-NMR; inhibition; phosphine; Concanavalin A; beta-galactosidase; dynamic drug discovery.
HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-12414 (URN)978-91-7415-618-8 (ISBN)
Disputas
2010-05-12, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (engelsk)
Opponent
Veileder
Merknad
QC 20100621Tilgjengelig fra: 2010-04-22 Laget: 2010-04-20 Sist oppdatert: 2010-11-29bibliografisk kontrollert
2. Photochemical Surface Functionalization: Synthesis, Nanochemistry and Glycobiological Studies
Åpne denne publikasjonen i ny fane eller vindu >>Photochemical Surface Functionalization: Synthesis, Nanochemistry and Glycobiological Studies
2011 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
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.

sted, utgiver, år, opplag, sider
Stockholm: KTH Royal Institute of Technology, 2011. s. 86
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2011:47
Emneord
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
HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-41973 (URN)978-91-7501-072-4 (ISBN)
Disputas
2011-10-21, F3, Lindstedtsvägen 26, KTH, Stockholm, 13:00 (engelsk)
Opponent
Veileder
Merknad
QC 20111004Tilgjengelig fra: 2011-10-04 Laget: 2011-10-04 Sist oppdatert: 2011-10-04bibliografisk kontrollert

Open Access i DiVA

Fulltekst mangler i DiVA

Andre lenker

Forlagets fulltekstScopus

Personposter BETA

Brinck, Tore

Søk i DiVA

Av forfatter/redaktør
Caraballo, RémiDeng, LingquanAmorim, LuisBrinck, ToreRamström, Olof
Av organisasjonen
I samme tidsskrift
Journal of Organic Chemistry

Søk utenfor DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric

doi
urn-nbn
Totalt: 204 treff
RefereraExporteraLink to record
Permanent link

Direct link
Referera
Referensformat
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Annet format
Fler format
Språk
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Annet språk
Fler språk
Utmatningsformat
  • html
  • text
  • asciidoc
  • rtf