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Stereospecific Ester Activation in Nitrite-Mediated Carbohydrate Epimerization
KTH, Skolan för kemivetenskap (CHE), Kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi.ORCID-id: 0000-0002-1533-6514
2006 (Engelska)Ingår i: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 71, nr 8, s. 3306-3309Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

The Lattrell-Dax method of nitrite-mediated substitution of carbohydrate triflates is an efficient method to generate structures of inverse configuration. In the present study, epimerization of gluco- and galactopyranoside derivatives to the corresponding allo- and gulopyranoside structures by triflation/nitrite treatment has been investigated. It was found that a neighboring ester group was essential for the reactivity of the nitrite-mediated triflate, inversion. Furthermore, a good inversion yield also depended on the relative configuration of the neighboring ester group to the triflate. Only with the ester group in the equatorial position, whatever the configuration of the triflate, did the reaction proceed smoothly, whereas a neighboring axial ester group proved largely inefficient. The results were subsequently used to predict the inversion of glucopyranoside derivatives to the mannopyranoside epimers.

Ort, förlag, år, upplaga, sidor
2006. Vol. 71, nr 8, s. 3306-3309
Nyckelord [en]
stereoselective-synthesis, glycosides, benzoate, anions, sugars
Nationell ämneskategori
Organisk kemi
Identifikatorer
URN: urn:nbn:se:kth:diva-9883DOI: 10.1021/jo052662iISI: 000236678100053PubMedID: 16599637Scopus ID: 2-s2.0-33645773127OAI: oai:DiVA.org:kth-9883DiVA, id: diva2:139843
Anmärkning
QC 20100709Tillgänglig från: 2009-01-27 Skapad: 2009-01-27 Senast uppdaterad: 2020-03-09Bibliografiskt granskad
Ingår i avhandling
1. Efficient Carbohydrate Synthesis By Intra- and Supramolecular Control
Öppna denna publikation i ny flik eller fönster >>Efficient Carbohydrate Synthesis By Intra- and Supramolecular Control
2009 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

The Lattrell-Dax method of nitrite-mediated substitution of carbohydrate triflates is an efficient method to generate structures of inverse configuration. In this study, the effects of the neighboring group on the Lattrell-Dax inversion were explored. A new carbohydrate/anion host-guest system was discovered and the ambident reactivity of the nitrite anion was found to cause a complicated behavior of the reaction. It has been demonstrated that a neighboring equatorial ester group plays a highly important role in this carbohydrate epimerization reaction, restricting the nitrite N-attack, thus resulting in O-attack only and inducing the formation of inversion compounds in good yields. Based on this effect, efficient synthetic routes to a range of carbohydrate structures, notably β-D-mannosides and β-D-talosides, were designed by use of double parallel and double serial inversion. A supramolecularly activated, triggered cascade reaction was also developed. This cascade reaction is triggered by a deprotonation process that is activated by anions. It was found that the anions can activate this reaction following their hydrogen bonding tendencies to the hydroxyl group in aprotic solvents.

Ort, förlag, år, upplaga, sidor
Stockholm: KTH, 2009. s. 59
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2009:2
Nyckelord
Carbohydrate Chemistry, Supramolecular Control, Ambident Reactivity
Nationell ämneskategori
Organisk kemi
Identifikatorer
urn:nbn:se:kth:diva-9882 (URN)978-91-7415-207-4 (ISBN)
Disputation
2009-02-05, F3, KTH, Lindstedtsvägen 26, Stockholm, 10:00 (Engelska)
Opponent
Handledare
Anmärkning
QC 20100709Tillgänglig från: 2009-01-27 Skapad: 2009-01-26 Senast uppdaterad: 2019-12-20Bibliografiskt granskad
2. Efficient carbohydrate synthesis by controlled inversion strategies
Öppna denna publikation i ny flik eller fönster >>Efficient carbohydrate synthesis by controlled inversion strategies
2006 (Engelska)Licentiatavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

The Lattrell-Dax method of nitrite-mediated substitution of carbohydrate triflates is an efficient method to generate structures of inverse configuration. In this study it has been demonstrated that a neighboring equatorial ester group plays a highly important role in this carbohydrate epimerization reaction, inducing the formation of inversion compounds in good yields. Based on this effect, efficient synthetic routes to a range of carbohydrate structures, notably β-D-mannosides and β-D-talosides, were designed. By use of the ester activation effect for neighboring groups, a double parallel as well as a double serial inversion strategy was developed.

Ort, förlag, år, upplaga, sidor
Stockholm: KTH, 2006. s. 40
Serie
Trita-IOK, ISSN 1100-7974 ; 107
Nyckelord
Carbohydrate Chemistry, Carbohydrate Protection, Epimerization, Inversion, Dynamic, Regioselective Control, Neighboring Group Participation
Nationell ämneskategori
Organisk kemi
Identifikatorer
urn:nbn:se:kth:diva-4179 (URN)91-7178-502-7 (ISBN)
Presentation
2006-11-30, E2, KTH, Lindstedtsvägen 3, Stockholm, 10:00
Handledare
Anmärkning
QC 20101111Tillgänglig från: 2006-11-22 Skapad: 2006-11-22 Senast uppdaterad: 2010-11-11Bibliografiskt granskad
3. Carbohydrate Synthesis and Study of Carbohydrate-Lectin Interactions Using QCM Biosensors and Microarray Technologies
Öppna denna publikation i ny flik eller fönster >>Carbohydrate Synthesis and Study of Carbohydrate-Lectin Interactions Using QCM Biosensors and Microarray Technologies
2006 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

Interactions between carbohydrates and proteins are increasingly being recognized as crucial in many biological processes, such as cellular adhesion and communication. In order to investigate the interactions of carbohydrates and proteins, the development of efficient analytic technologies, as well as novel strategies for the synthesis of carbohydrates, have to be explored. To date, several methods have been exploited to analyze interactions of carbohydrates and proteins, for example, biosensors, nuclear magnetic resonance (NMR); enzyme-linked immunosorbent assays (ELISA), X-ray crystallography and array technologies. This thesis describes the development of novel strategies for the synthesis of carbohydrates, as well as new efficient strategies to Quartz Crystal Microbalance- (QCM-) biosensors and carbohydrate microarrays technologies. These methodologies have been used to probe carbohydrate-lectin-interactions for a range of plant and animal lectins.

Ort, förlag, år, upplaga, sidor
Stockholm: KTH, 2006. s. 106
Serie
Trita-IOK, ISSN 1100-7974 ; 2006:106
Nyckelord
Lectins; Carbohydrates; Molecular recognition; Biosensors; Quartz crystal microbalance; Carbohydrate microarrays.
Nationell ämneskategori
Organisk kemi
Identifikatorer
urn:nbn:se:kth:diva-4177 (URN)91-7178-503-5 (ISBN)
Disputation
2006-12-01, D3, Lindstedtsvägen 5, Stockholm, 10:00
Opponent
Handledare
Anmärkning
QC 20100915Tillgänglig från: 2006-11-22 Skapad: 2006-11-22 Senast uppdaterad: 2019-12-20Bibliografiskt granskad

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