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Phosphine-catalyzed disulfide metathesis
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, Organic Chemistry.ORCID iD: 0000-0003-2673-075X
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2008 (English)In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, no 48, 6603-6605 p.Article in journal (Refereed) Published
Abstract [en]

The reaction between disulfides and phosphines generates a reversible disulfide metathesis process.

Place, publisher, year, edition, pages
2008. no 48, 6603-6605 p.
Keyword [en]
DYNAMIC COMBINATORIAL CHEMISTRY, ORGANIC SULFUR CHEMISTRY, EXCHANGE-REACTION, PHOSPHORUS NUCLEOPHILES, EQUILIBRIUM-CONSTANTS, INTERCHANGE REACTIONS, DRUG DISCOVERY, BOND FORMATION, LIBRARIES, WATER
Identifiers
URN: urn:nbn:se:kth:diva-12443DOI: 10.1039/b815710cISI: 000261742500041Scopus ID: 2-s2.0-57249086290OAI: oai:DiVA.org:kth-12443DiVA: diva2:311713
Note

QC20100621

Available from: 2010-04-22 Created: 2010-04-22 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

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Brinck, Tore

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