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Oligosaccharide Synthesis (oligosaccharide + synthesis)

Distribution by Scientific Domains
Chemistry100%

Selected Abstracts

S-Benzoxazolyl (SBox) Glycosides in Oligosaccharide Synthesis: Novel Glycosylation Approach to the Synthesis of ,-D-Glucosides, ,-D-Galactosides, and ,-D-Mannosides.

CHEMINFORM, Issue 47 2003
Alexei V. Demchenko
No abstract is available for this article. [source]

Low-Concentration 1,2- trans ,-Selective Glycosylation Strategy and Its Applications in Oligosaccharide Synthesis

CHEMISTRY - A EUROPEAN JOURNAL, Issue 41 2009
Chin-Sheng Chao
Abstract This study develops an operationally easy, efficient, and general 1,2- trans ,-selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent ,-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2- trans ,-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2- trans ,-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant ,-(1,6)-glucan trisaccharide, ,-linked Gb3 and isoGb3 derivatives. [source]

S- Thiazolinyl (STaz) Glycosides as Versatile Building Blocks for Convergent Selective, Chemoselective, and Orthogonal Oligosaccharide Synthesis

CHEMISTRY - A EUROPEAN JOURNAL, Issue 25 2006
Papapida Pornsuriyasak
Abstract In the aim of developing new procedures for efficient oligosaccharide assembly, a range of S- thiazolinyl (STaz) glycosides have been synthesized. These novel derivatives were evaluated against a variety of reaction conditions and were shown to be capable of being chemoselectively activated in the armed,disarmed fashion. Moreover, the S- thiazolinyl moiety exhibited a remarkable propensity for selective activation over other common leaving groups. Conversely, a variety of leaving groups could be selectively activated over the STaz moiety, which, in turn, allowed STaz/S- ethyl and STaz/S- phenyl orthogonal approaches. To demonstrate versatility of novel STaz derivatives, a number of oligosaccharide targets have been synthesized in a convergent selective, orthogonal, and chemoselective fashion. [source]

Low-Concentration 1,2- trans ,-Selective Glycosylation Strategy and Its Applications in Oligosaccharide Synthesis

CHEMISTRY - A EUROPEAN JOURNAL, Issue 41 2009
Chin-Sheng Chao
Abstract This study develops an operationally easy, efficient, and general 1,2- trans ,-selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent ,-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2- trans ,-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2- trans ,-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant ,-(1,6)-glucan trisaccharide, ,-linked Gb3 and isoGb3 derivatives. [source]

Going to Extremes: "Super" Armed Glycosyl Donors in Glycosylation Chemistry

CHEMISTRY - A EUROPEAN JOURNAL, Issue 27 2007
Henrik
Abstract This concept article gives an overview of stereoelectronic effects in monosaccharide systems and how these can be used to dramatically enhance the reactivity of glycosyl donors in oligosaccharide synthesis. [source]

Preparation and Use of Microarrays Containing Synthetic Heparin Oligosaccharides for the Rapid Analysis of Heparin,Protein Interactions

CHEMISTRY - A EUROPEAN JOURNAL, Issue 34 2006
Christian Noti
Abstract Heparin is a highly sulfated, linear polymer that participates in a plethora of biological processes by interaction with many proteins. The chemical complexity and heterogeneity of this polysaccharide can explain the fact that, despite its widespread medical use as an anticoagulant drug, the structure,function relationship of defined heparin sequences is still poorly understood. Here, we present the chemical synthesis of a library containing heparin oligosaccharides ranging from di- to hexamers of different sequences and sulfation patterns. An amine-terminated linker was placed at the reducing end of the synthetic structures to allow for immobilization onto N -hydroxysuccinimide activated glass slides and creation of heparin microarrays. Key features of this modular synthesis, such as the influence of the amine linker on the glycosidation efficiency, the use of 2-azidoglucose as glycosylating agents for oligosaccharide assembly, and the compatibility of the protecting group strategy with the sulfation-deprotection steps, are discussed. Heparin microarrays containing this oligosaccharide library were constructed using a robotic printer and employed to characterize the carbohydrate binding affinities of three heparin-binding growth factors. FGF-1, FGF-2 and FGF-4 that are implicated in angiogenesis, cell growth and differentiation were studied. These heparin chips aided in the discovery of novel, sulfated sequences that bind FGF, and in the determination of the structural requirements needed for recognition by using picomoles of protein on a single slide. The results presented here highlight the potential of combining oligosaccharide synthesis and carbohydrate microarray technology to establish a structure,activity relationship in biological processes. [source]