Efficient Chemoenzymatic Synthesis of N-Glycans with a β1,4-Galactosylated Bisecting GlcNAc Motif

被引:11
|
作者
Weiss, Michael [1 ]
Ott, Dimitri [1 ]
Karagiannis, Theodoros [1 ]
Weishaupt, Markus [1 ]
Niemietz, Mathaeus [1 ]
Eller, Steffen [1 ]
Lott, Marie [1 ]
Martinez-Orts, Monica [2 ]
Canales, Angeles [2 ]
Razi, Nahid [3 ,4 ]
Paulson, James [3 ,4 ]
Unverzagt, Carlo [1 ]
机构
[1] Univ Bayreuth, Bioorgan Chem, Univ Str 30, D-95447 Bayreuth, Germany
[2] Univ Complutense Madrid, Dept Quim Organ 1, Fac Ciencias Quim, Avd Complutense S-N, Madrid 28040, Spain
[3] Scripps Res Inst, Dept Mol Med, 10550 N Torrey Pines Rd, La Jolla, CA 92037 USA
[4] Scripps Res Inst, Dept Immunol & Microbiol, 10550 N Torrey Pines Rd, La Jolla, CA 92037 USA
基金
美国国家卫生研究院;
关键词
N-glycans; glycosylation; glycobiology; immunoglobulin; paramagnetic NMR spectroscopy; COMPLEX; IGG; OLIGOSACCHARIDES; GALACTOSE; BREAKING; BRANCH; FUCOSE; CORE;
D O I
10.1002/cbic.202000268
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
In human serum immunoglobulin G (IgG), a rare modification of biantennary complex N-glycans lead to a beta 1,4-galactosylated bisecting GlcNAc branch. We found that the bisecting GlcNAc on a biantennary core-fucosylated N-glycan was enzymatically galactosylated under stringent reaction conditions. Further optimizations led to an efficient enzymatic approach to this particular modification for biantennary substrates. Notably, tri- and tetra-antennary complex N-glycans were not converted by bovine galactosyltransferase. An N-glycan with a galactosylated bisecting GlcNAc was linked to a lanthanide binding tag. The pseudo-contact shifts (PCS) obtained from the corresponding Dy-complex were used to calculate the conformational preferences of the rare N-glycan. Besides two extended conformations only a single folded conformation was found.
引用
收藏
页码:3212 / 3215
页数:4
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