“Cap-Tag”—Novel Methods for the Rapid Purification of Oligosaccharides Prepared by Automated Solid-Phase Synthesis

Palmacci, Emma R.; Hewitt, Michael C.; Seeberger, Peter H.

doi:10.1002/1521-3757(20011203)113:23<4565::aid-ange4565>3.0.co;2-2

Cited by 45 publications

(52 citation statements)

References 23 publications

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“…33 After resin cleavage, the desired sequence was separated from fluorous byproducts by HPLC. A much cleaner trisaccharide 14 was prepared by the fluorous capping strategy as compared to a similar synthesis without fluorous capping, where a significant amount of deletion sequences (n-l and n-2) was observed.…”

Section: Solid-phase Synthesis With Fluorous Capping Agentsmentioning

confidence: 99%

Fluorous Chemistry for Synthesis and Purification of Biomolecules: Peptides, Oligosaccharides, Glycopeptides, and Oligonucleotides

Zhang

2007

Current Fluoroorganic Chemistry

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Fluorous chemistry has advanced well beyond the scope of biphasic catalysis and high-throughput synthesis of small molecules. This review describes the recent development of fluorous technologies in the synthesis and purification of biomolecules including peptides, oligosaccharides, glycopeptides, and oligonucleotides.Highly fluorinated (fluorous) molecules are lipophobic and hydrophobic, 1 but they have strong interaction with fluorous separation media. This unique property has been exploited for phase separation of fluorous-tagged molecules from non-fluorous molecules by liquid-liquid extraction (LLE) with fluorous solvents or by solid-phase extraction (SPE) and chromatography with fluorous silica gel. 2 In 1994 Horváth and Rábai introduced the concept of "fluorous biphasic catalysis" for catalyst recovery. 3,4 Since then, Curran group at the University of Pittsburgh, Fluorous Technologies, Inc., and others have developed a large collection of fluorous catalysts, reagents, scavengers, protecting groups for "fluorous synthesis" of small molecules. 5 ' 8 Now fluorous technologies have been applied to synthesis arid separation of biomolecules.

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Section: Solid-phase Synthesis With Fluorous Capping Agentsmentioning

confidence: 99%

Fluorous Chemistry for Synthesis and Purification of Biomolecules: Peptides, Oligosaccharides, Glycopeptides, and Oligonucleotides

Zhang

2007

Current Fluoroorganic Chemistry

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“…However, unlike tags with multiple fluorocarbon chains, the fluorous group did not prevent the use of standard chromatography methods if necessary. A related fluorous silyl group has been used not in iterative synthesis but to cap oligosaccharides made on solid-phase for isolation of tagged sequences by SPE (18). More recently, a fluorous version of a carbamate nitrogen protecting group was developed and applied to the synthesis of a disaccharide 6 ( Figure 4) (19).…”

Section: Fluorous Tags For Solid-phase Extraction In Carbohydrate Synmentioning

confidence: 99%

Carbohydrate Microarrays and Fluorous-Phase Synthesis: Interfacing Fluorous-Phase Tags with the Direct Formation of Glycoarrays

Pohl

2007

Current Fluoroorganic Chemistry

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Phase switching, such as the use of fluorocarbon tags, is a common technique to facilitate purification of intermediates in iterative biopolymer synthesis. After a review of the application of fluorous tags in carbohydrate synthesis, a new method to directly array sugars via noncovalent fluorousfluorous interactions is discussed. Light-fluorous tags now can serve not only to simplify iterative oligosaccharide synthesis, but also to directly pattern sugars on surfaces for biological screening.

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“…The fluorous tagging strategy has been introduced to make reagents [8][9][10][11], scavengers [12][13][14][15][16], protecting groups [17][18][19][20][21] and related tags [22][23] for parallel and mixture syntheses [24][25][26][27][28]. It has also been used in peptide and oligosaccharide syntheses [29][30][31].…”

Section: Introductionmentioning

confidence: 99%

Fluorous parallel synthesis of a hydantoin/thiohydantoin library

Zhang

2005

Mol Divers

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Fluorous tagging strategy is applied to solution-phase parallel synthesis of a library containing hydantoin and thiohydantoin analogs. Two perfluoroalkyl (Rf)-tagged α-amino esters each react with 6 aromatic aldehydes under reductive amination conditions. Twelve amino esters then each react with 10 isocyanates and isothiocyanates in parallel. The resulting 120 ureas and thioureas undergo spontaneous cyclization to form the corresponding hydantoins and thiohydantoins. The intermediate and final product purifications are performed with solid-phase extraction (SPE) over FluoroFlash™ cartridges, no chromatography is required. Using standard instruments and straightforward SPE technique, one chemist accomplished the 120-member library synthesis in less than 5 working days, including starting material synthesis and product analysis.

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“Cap-Tag”—Novel Methods for the Rapid Purification of Oligosaccharides Prepared by Automated Solid-Phase Synthesis

Cited by 45 publications

References 23 publications

Fluorous Chemistry for Synthesis and Purification of Biomolecules: Peptides, Oligosaccharides, Glycopeptides, and Oligonucleotides

Fluorous Chemistry for Synthesis and Purification of Biomolecules: Peptides, Oligosaccharides, Glycopeptides, and Oligonucleotides

Carbohydrate Microarrays and Fluorous-Phase Synthesis: Interfacing Fluorous-Phase Tags with the Direct Formation of Glycoarrays

Fluorous parallel synthesis of a hydantoin/thiohydantoin library

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