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咪唑鎓标记的唾液乳糖胺探针的化学酶法合成

Chemo-enzymatic synthesis of imidazolium-tagged sialyllactosamine probes.

作者信息

Sittel Imke, Galan M Carmen

机构信息

School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.

School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, UK.

出版信息

Bioorg Med Chem Lett. 2015 Oct 1;25(19):4329-32. doi: 10.1016/j.bmcl.2015.07.049. Epub 2015 Aug 5.

DOI:10.1016/j.bmcl.2015.07.049
PMID:26318990
Abstract

Two novel α-linked sialyltrisaccharide imidazolium-type probes (ITags) based on the structures of biologically relevant 6'-sialyllactosamine and 3'-sialyllactosamine were efficiently and stereoselectively prepared using a chemo-enzymatic approach. The apparent kinetic parameters for the enzyme catalyzed transformations with α-2,3-sialyltransferase (α-2,3-ST) and α-2,6-sialyltransferase (α-2,6-ST) were measured by LC-MS using the ionic probes. This strategy demonstrates the suitability of the ITags to probe glycosyltransferase activity and their versatility in the preparation of sialylated epitopes for glycobiology research.

摘要

基于具有生物学相关性的6'-唾液酸乳糖胺和3'-唾液酸乳糖胺结构,通过化学酶法高效且立体选择性地制备了两种新型α-连接的唾液酸三糖咪唑鎓型探针(ITags)。使用离子探针通过液相色谱-质谱法测定了α-2,3-唾液酸转移酶(α-2,3-ST)和α-2,6-唾液酸转移酶(α-2,6-ST)催化转化的表观动力学参数。该策略证明了ITags适用于探测糖基转移酶活性及其在制备用于糖生物学研究的唾液酸化表位方面的多功能性。

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Chemo-enzymatic synthesis of imidazolium-tagged sialyllactosamine probes.咪唑鎓标记的唾液乳糖胺探针的化学酶法合成
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