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Phosphine-catalyzed disulfide metathesis
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, Organisk kemi.ORCID-id: 0000-0003-2673-075X
Visa övriga samt affilieringar
2008 (Engelska)Ingår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, nr 48, s. 6603-6605Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

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

Ort, förlag, år, upplaga, sidor
2008. nr 48, s. 6603-6605
Nyckelord [en]
DYNAMIC COMBINATORIAL CHEMISTRY, ORGANIC SULFUR CHEMISTRY, EXCHANGE-REACTION, PHOSPHORUS NUCLEOPHILES, EQUILIBRIUM-CONSTANTS, INTERCHANGE REACTIONS, DRUG DISCOVERY, BOND FORMATION, LIBRARIES, WATER
Identifikatorer
URN: urn:nbn:se:kth:diva-12443DOI: 10.1039/b815710cISI: 000261742500041Scopus ID: 2-s2.0-57249086290OAI: oai:DiVA.org:kth-12443DiVA, id: diva2:311713
Anmärkning

QC20100621

Tillgänglig från: 2010-04-22 Skapad: 2010-04-22 Senast uppdaterad: 2017-12-12Bibliografiskt granskad
Ingår i avhandling
1. Dynamic Sulfur Chemistry: Screening, Evaluation and Catalysis
Öppna denna publikation i ny flik eller fönster >>Dynamic Sulfur Chemistry: Screening, Evaluation and Catalysis
2010 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Stockholm: KTH, 2010. s. 84
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2010:14
Nyckelord
Dynamic combinatorial chemistry; dynamic sulfur chemistry; thioglycoside; mutarotation; disulfide metathesis; hemithioacetal formation; 1H STD-NMR; inhibition; phosphine; Concanavalin A; beta-galactosidase; dynamic drug discovery.
Nationell ämneskategori
Kemi Organisk kemi Organisk kemi
Identifikatorer
urn:nbn:se:kth:diva-12414 (URN)978-91-7415-618-8 (ISBN)
Disputation
2010-05-12, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (Engelska)
Opponent
Handledare
Anmärkning
QC 20100621Tillgänglig från: 2010-04-22 Skapad: 2010-04-20 Senast uppdaterad: 2010-11-29Bibliografiskt granskad

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Brinck, Tore

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Caraballo, RemiRahm, MartinVongvilai, PornrapeeBrinck, ToreRamström, Olof
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