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HPLC-assisted Automated Oligosaccharide Synthesis

Overview
Journal Org Lett
Specialties Biochemistry
Chemistry
Date 2012 Jun 1
PMID 22646669
Citations 34
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Abstract

A standard HPLC was adapted to polymer supported oligosaccharide synthesis. Solution-based reagents are delivered using a software-controlled solvent delivery system. The reaction progress and completion can be monitored in real time using a standard UV detector. All steps of oligosaccharide assembly including loading, glycosylation, deprotection, and cleavage can be performed using this setup.

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References
1.
Boltje T, Kim J, Park J, Boons G . Chiral-auxiliary-mediated 1,2-cis-glycosylations for the solid-supported synthesis of a biologically important branched alpha-glucan. Nat Chem. 2010; 2(7):552-7. PMC: 2892400. DOI: 10.1038/nchem.663. View

2.
Tran A, Burden R, Racys D, Galan M . Ionic catch and release oligosaccharide synthesis (ICROS). Chem Commun (Camb). 2011; 47(15):4526-8. DOI: 10.1039/c0cc05580h. View

3.
Sears P, Wong C . Toward automated synthesis of oligosaccharides and glycoproteins. Science. 2001; 291(5512):2344-50. DOI: 10.1126/science.1058899. View

4.
Wu X, Grathwohl M, Schmidt R . Efficient solid-phase synthesis of a complex, branched N-glycan hexasaccharide: use of a novel linker and temporary-protecting-group pattern. Angew Chem Int Ed Engl. 2002; 41(23):4489-93. DOI: 10.1002/1521-3773(20021202)41:23<4489::AID-ANIE4489>3.0.CO;2-X. View

5.
Jonke S, Liu K, Schmidt R . Solid-phase oligosaccharide synthesis of a small library of N-glycans. Chemistry. 2005; 12(4):1274-90. DOI: 10.1002/chem.200500707. View