Divergent Chemoenzymatic Synthesis of Asymmetrical-Core-Fucosylated and Core-Unmodified N-Glycans

Li Tiehai; Huang Min; Liu Lin; Wang Shuo; Moremen Kelley W.; Boons Geert-Jan

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Divergent Chemoenzymatic Synthesis of Asymmetrical-Core-Fucosylated and Core-Unmodified N-Glycans

机译：不对称核心岩藻糖基化和核心未修饰的N-聚糖的不同化学酶法合成

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A divergent chemoenzymaytic approach for the preparation of core-fucosylated and core-unmodified asymmetrical N-glycans from a common advances precursor is described. An undecasaccharide was synthesized by sequential chemical glycosylations of an orthogonally protected core fucosylated hexasaccharide that is common to all mammalian core fucosylated N-glycans. Antennae-selective enzymatic extension of the undecasaccharide using a panel of glycosyl transferases afforded core fucosylated asymmetrical triantennary N-glycan isomers, which are potential biomarkers for breast cancer. A unique aspect of our approach is that a fucosidase (FucA1) has been identified that selectively can cleave a core-fucoside without affecting the fucoside of a sialyl LewisX epitope to give easy access to core-unmodified compounds.

机译：描述了一种从常规进展前体制备核心岩藻糖基化和核心未修饰的不对称N-聚糖的化学趋化方法。通过对所有哺乳动物核心岩藻糖基化的N-聚糖共有的正交保护的核心岩藻糖基化六糖进行连续化学糖基化合成十一碳糖。使用一组糖基转移酶对十一碳糖进行天线选择性酶促延伸，可提供岩藻糖基化的不对称三天线N-聚糖异构体核心，这是乳腺癌的潜在生物标记。我们方法的一个独特方面是已鉴定出岩藻糖苷酶（FucA1），可以选择性地裂解核心岩藻糖苷，而不会影响唾液酸LewisX表位的岩藻糖苷，从而可轻松获得未修饰的核心化合物。

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《Chemistry: A European journal》 |2016年第52期|共5页
作者
Li Tiehai; Huang Min; Liu Lin; Wang Shuo; Moremen Kelley W.; Boons Geert-Jan;
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正文语种 eng
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关键词
asymmetrical synthesis; bioorganic chemistry; chemoenzymatic synthesis; glycosylation; N-glycans;

机译：不对称合成;生物有机化学;化学酶法合成;糖基化;N-聚糖;

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1. Divergent Chemoenzymatic Synthesis of Asymmetrical-Core-Fucosylated and Core-Unmodified N-Glycans [J] . Li Tiehai, Huang Min, Liu Lin, Chemistry: A European journal . 2016,第52期

机译：不对称核心岩藻糖基化和核心未修饰的N-聚糖的不同化学酶法合成
2. Chemoenzymatic synthesis of glycopeptidesbearing rare N-glycan sequences with or withoutbisecting GlcNAc [J] . Weizhun Yang, Sherif Ramadan, Jared Orwenyo, Chemical science . 2018,第43期

机译：带有或不带有对分的GlcNAc的带有稀有N-聚糖序列的糖肽的化学合成
3. Chemoenzymatic Synthesis of N-glycan Positional Isomers and Evidence for Branch Selective Binding by Monoclonal Antibodies and Human C-type Lectin Receptors [J] . Echeverria Begona, Serna Sonia, Achilli Silvia, ACS Chemical Biology . 2018,第8期

机译：N-聚糖位置异构体的化学酶合成及单克隆抗体和人C型凝集素受体分支选择性结合的证据
4. CHEMOENZYMATIC SYNTHESIS AND CHARACTERIZATION OF PARAMAGNETIC MULTIANTENNARY N-GLYCAN COMPLEXES [C] . T. Karagiannis, M. Monnich, L. Perkams International Carbohydrate Symposium . 2018

机译：顺磁性多银N-聚糖络合物的化学酶合成与表征
5. Chemoenzymatic synthesis of Amaryllidaceae alkaloids and their C-1 analogues. Symmetry based approach to total synthesis of thebaine. [D] . Collins, Jonathan A. 2010

机译：化学酶法合成金缕梅生物碱及其C-1类似物。基于对称性的蒂巴因全合成方法。
6. Divergent Chemoenzymatic Synthesis of Asymmetrical-Core-Fucosylated and Core-Unmodified N-Glycans [O] . Dr. Tiehai Li, Dr. Min Huang, Dr. Lin Liu, -1

机译：不对称核心岩藻糖基化和核心未修饰的N-聚糖的不同化学酶法合成
7. Efficient Chemoenzymatic Synthesis of an N-glycan Isomer Library [O] . Li, Lei, Liu, Yunpeng, Ma, Cheng, 2015

机译：N-聚糖异构体库的高效化学合成

Divergent Chemoenzymatic Synthesis of Asymmetrical-Core-Fucosylated and Core-Unmodified N-Glycans

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