title: Glycosylation efficiencies on different solid supports using a hydrogenolysis-labile linker.
abstract: Automated oligosaccharide assembly requires suitable linkers to connect the first monosaccharide to a solid support. A new hydrogenolysis-labile linker that is stable under both acidic and basic conditions was designed, synthesized and coupled to different resins. Glycosylation and cleavage efficiencies on these functionalized solid supports were investigated, and restrictions for the choice of solid support for oligosaccharide synthesis were found.
authors: Department of Biomolecular Systems, Max Planck Institute of Colloids and Interfaces, Am Mühlenberg 1, 14776 Potsdam, Germany ; Institut für Chemie und Biochemie, Freie Universität Berlin, Arnimallee 22, 14195 Berlin, Germany.
authors: Mayeul
authors: M
authors: Collot
authors: Steffen
authors: S
authors: Eller
authors: Markus
authors: M
authors: Weishaupt
authors: Peter H
authors: PH
authors: Seeberger
keywords: glycosylation; hydrogenolysis; linkers; oligosaccharides; resins; solid-phase synthesis
references: Beilstein J Org Chem. 2012;8:2067-71
references: 23209541
references: Nature. 1965 Jul 31;207(996):522-3
references: 5886140
references: J Am Chem Soc. 2005 Sep 28;127(38):13162-3
references: 16173741
references: J Org Chem. 2007 Jun 8;72(12):4367-77
references: 17503844
references: Chem Rev. 2000 Oct 11;100(10):3859
references: 11749330
references: Chem Rev. 2000 Dec 13;100(12):4349-94
references: 11749351
references: Angew Chem Int Ed Engl. 2012 Apr 27;51(18):4393-6
references: 22334421
references: Science. 2001 Feb 23;291(5508):1523-7
references: 11222853
references: J Org Chem. 1997 Jan 24;62(2):411-416
references: 11671417
references: J Pept Sci. 1995 Jan-Feb;1(1):31-44
references: 9222982
references: J Comb Chem. 2006 Mar-Apr;8(2):213-20
references: 16529516
references: Org Lett. 2002 Nov 28;4(24):4213-6
references: 12443061
references: Angew Chem Int Ed Engl. 2007;46(22):4173-5
references: 17444542
references: Science. 1985 Oct 18;230(4723):281-5
references: 3863253
references: Org Biomol Chem. 2007 Jul 21;5(14):2189-200
references: 17609746
references: Curr Opin Chem Biol. 2001 Jun;5(3):264-8
references: 11479117
references: Chemistry. 2004 Feb 20;10(4):1007-13
references: 14978827
references: Chemistry. 2006 Nov 24;12(34):8664-86
references: 17066397
references: J Am Chem Soc. 2009 Nov 25;131(46):16669-71
references: 19886622
references: J Comb Chem. 2001 Jan-Feb;3(1):117-24
references: 11148072
references: Org Lett. 2012 Jul 20;14(14):3776-9
references: 22780913
references: Biopolymers. 1998;47(5):365-80
references: 9973867
references: J Am Chem Soc. 1966 Nov 20;88(22):5319-24
references: 5979268