Roger B. Ruggeri

Bio: Roger B. Ruggeri is an academic researcher from Yale University. The author has contributed to research in topics: Glycosidic bond & Silyl ether. The author has an hindex of 2, co-authored 2 publications receiving 276 citations.

A strategy for the solid-phase synthesis of oligosaccharides

Abstract: Repeating glycosidic linkages of oligosaccharides can be synthesized by solid-phase methods. Glycals were attached to a polystyrene copolymer with a silyl ether bond and were activated to function as glycosyl donors with 3,3-dimethyldioxirane. Glycosidation was performed by reactions with a solution-based acceptor (itself a glycal). Excess acceptor and promoter were removed by rinsing after each coupling, and the desired oligosaccharides were then easily obtained from the polymer by the addition of tetra-n-butylammonium fluoride. By this method, glycosidations are stereospecific and interior deletions are avoided.

A Strategy for the Solid-Phase Synthesis of Oligosaccharides.

Abstract: Repeating glycosidic linkages of oligosaccharides can be synthesized by solid-phase methods. Glycals were attached to a polystyrene copolymer with a silyl ether bond and were activated to function as glycosyl donors with 3,3-dimethyldioxirane. Glycosidation was performed by reactions with a solution-based acceptor (itself a glycal). Excess acceptor and promoter were removed by rinsing after each coupling, and the desired oligosaccharides were then easily obtained from the polymer by the addition of tetra-n-butylammonium fluoride. By this method, glycosidations are stereospecific and interior deletions are avoided.

Automated Solid-Phase Synthesis of Oligosaccharides

Abstract: Traditionally, access to structurally defined complex carbohydrates has been very laborious Although recent advancements in solid-phase synthesis have made the construction of complex oligosaccharides less tedious, a high level of technical expertise is still necessary to obtain the desired structures We describe the automated chemical synthesis of several oligosaccharides on a solid-phase synthesizer A branched dodecasaccharide was synthesized through the use of glycosyl phosphate building blocks and an octenediol functionalized resin The target oligosaccharide was readily obtained after cleavage from the solid support Access to certain complex oligosaccharides now has become feasible in a fashion much like the construction of oligopeptides and oligonucleotides

New principles for glycoside-bond formation.

Abstract: Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.

The “One-Bead-One-Compound” Combinatorial Library Method

Abstract: 1. Peptoids 419 2. Oligocarbamates 420 3. Oligoureas 420 4. Vinylogous Sulfonyl Peptides 420 5. Peptidosulfonamides 420 6. Azatides 420 7. Ketides 420 D. Small Molecule Libraries 420 1. Acyclic Libraries 422 2. Libraries on Preformed Scaffolds 422 3. Heterocyclic Libraries 423 4. Structurally Heterogeneous Libraries 427 E. Cleavable Linkers 428 1. Single Cleavable Linkers 428 2. Multiply Cleavable Linkers 429 IV. Screening Methods 432 A. On-Bead Screening 432 1. Binding Assay 432 2. Functional Assay 434 B. Solution-Phase Screening 434 1. The 96-Well Two-Stage Releasable Assays 435

Toward automated synthesis of oligosaccharides and glycoproteins.

Abstract: The discovery of previously unknown functions associated with carbohydrates and the study of their structure-function relations are of current interest in carbohydrate chemistry and biology. Progress in this area is, however, hampered by the lack of convenient and effective tools for the synthesis and analysis of oligosaccharides and glycoconjugates. Development of automated synthesis of such materials is necessary to facilitate research in this field. This review describes recent advances in carbohydrate synthesis, with particular focus on developments that have potential application to the automated synthesis of oligosaccharides, glycopeptides, and glycoproteins.

Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries.

Abstract: Preface. Contributors. Solid--Phase Carbohydrate Synthesis: The Early Work (W.--C. Haase & P. Seeberger). The Glycal Assembly Method on Solid Supports: Synthesis of Oligosaccharides and Glycoconjugates (P. Cirillo & S. Danishefsky). The Sulfoxide Glycosylation Method and its Application to Solid--Phase Oligosaccharide Synthesis and the Generation of Combinatorial Libraries (C. Taylor). The Use of O--Glycosyl Trichloroacetimidates for the Polymer--Supported Synthesis of Oligosaccharides (L. Knerr & R. Schmidt). Synthesis of Oligosaccharides on Solid Support Using Thioglycosides and Pentenyl Glycosides (V. Wittmann). Solid--Phase Oligosaccharide Synthesis Using Glycosyl Phosphates (W.--C. Haase, et al.). Stereoselective beta--Mannosylation on Polymer Support (Y. Ito & H. Ando). Tools for "On--Bead" Monitoring and Analysis in Solid--Phase Oligosaccharide Synthesis (W.--C. Haase, et al.). Polyethyleneglycol omega--Monomethylether (MPEG)--Supported Solution--Phase Synthesis of Oligosaccharides (J. Krepinsky & S. Douglas). Two--Direction Glycosylations for the Preparation of Libraries of Oligosaccharides (G.--J. Boons & T. Zhu). Carbohydrate Libraries in Solution Using Thioglycosides: From Multistep Synthesis to Programmable, One--Pot Synthesis (E. Simanek & C.--H. Wong). Carbohydrate Libraries by the Random Glycosylation Approach (O. Kanie & O. Hindsgaul). Solid--Phase Synthesis of Biologically Important Glycopeptides (N. Bezay & H. Kunz). Preparation and Screening of Glycopeptide Libraries (P. St. Hilaire, et al.). Index.