Synthesis of a core trisaccharide building block for the assembly of N-glycan neoconjugates

作者: Sonia Serna , Bharat Kardak , Niels-Christian Reichardt , Manuel Martin-Lomas

DOI: 10.1016/J.TETASY.2009.02.028

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摘要: Abstract A short and high yielding synthesis of a core trisaccharide 1 as the key building block in assembly library N -glycan neoconjugates is presented. The β- d -Manp-(1→4)- -GlcpNAc linkage was introduced by inversion C-2 position β-glucoside. glucosyl donor efficiently synthesised following recently published one-pot strategy. 2-Naphthylmethyl benzylidene-acetal protection terminal mannose permitted selective liberation main branching sites for subsequent glycosylation. C5 azido linker attached to anomeric position, which stable throughout synthesis, will allow posterior immobilisation deprotected glycans on microarray surface.

参考文章(39)
Jeffrey D Esko, Ajit Varki, Gerald W Hart, Pamela Stanley, Carolyn R Bertozzi, Richard D Cummings, Marilynn E Etzler, Hudson H Freeze, Essentials of Glycobiology ,(1999)
Bing Li, Ying Zeng, Steven Hauser, Haijing Song, Lai-Xi Wang, Highly efficient endoglycosidase-catalyzed synthesis of glycopeptides using oligosaccharide oxazolines as donor substrates. Journal of the American Chemical Society. ,vol. 127, pp. 9692- 9693 ,(2005) , 10.1021/JA051715A
Mihirbaran Mandal, Vadim Y. Dudkin, Xudong Geng, Samuel J. Danishefsky, In pursuit of carbohydrate-based HIV vaccines, part 1: The total synthesis of hybrid-type gp120 fragments. Angewandte Chemie. ,vol. 43, pp. 2557- 2561 ,(2004) , 10.1002/ANIE.200353625
Alois Fürstner, Ingo Konetzki, A practical synthesis of β-d-mannopyranosides Tetrahedron Letters. ,vol. 39, pp. 5721- 5724 ,(1998) , 10.1016/S0040-4039(98)01163-0
Joachim Seifert, Matthias Lergenmüller, Yukishige Ito, Synthesis of anα-(2,3)-Sialylated, Complex-Type Undecasaccharide Angewandte Chemie International Edition. ,vol. 39, pp. 531- 534 ,(2000) , 10.1002/(SICI)1521-3773(20000204)39:3<531::AID-ANIE531>3.0.CO;2-F
Jie Xia, Saeed A Abbas, Robert D Locke, Conrad F Piskorz, James L Alderfer, Khushi L Matta, Use of 1,2-dichloro 4,5-dicyanoquinone (DDQ) for cleavage of the 2-naphthylmethyl (NAP) group Tetrahedron Letters. ,vol. 41, pp. 169- 173 ,(2000) , 10.1016/S0040-4039(99)02046-8
Thomas W.D.F. Rising, Timothy D.W. Claridge, Nicola Davies, David P. Gamblin, James W.B. Moir, Antony J. Fairbanks, Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation. Carbohydrate Research. ,vol. 341, pp. 1574- 1596 ,(2006) , 10.1016/J.CARRES.2006.03.007
Carlo Unverzagt, A Modular System for the Synthesis of Complex N‐Glycans Angewandte Chemie. ,vol. 36, pp. 1989- 1992 ,(1997) , 10.1002/ANIE.199719891