Sequential One-Pot Multienzyme Chemoenzymatic Synthesis of Glycosphingolipid Glycans.

Sequential One-Pot Multienzyme Chemoenzymatic Synthesis of Glycosphingolipid Glycans.
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顺序的一锅多酶化学酶合成的糖果糖聚糖。

DOI:
10.1021/acs.joc.6b01905
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发表时间:
2016-11-18
期刊:
The Journal of organic chemistry
影响因子:
--
通讯作者:
Chen X
Chen X
中科院分区:
其他
文献类型:
--
作者:
Yu H;Li Y;Zeng J;Thon V;Nguyen DM;Ly T;Kuang HY;Ngo A;Chen X

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鞘糖脂是生物学上重要的糖脂的一个不同的家族。除了脂质组分的变化外,还对300多种鞘糖脂聚糖进行了表征。这些聚糖直接参与各种分子识别事件。在含唾液酸的鞘糖脂(即神经节苷脂)中发现了几种天然存在的唾液酸形式。然而,目前还没有含有不太常见的唾液酸形式的神经节苷脂聚糖。在本文中,高效的一锅多酶(OPME)系统连续用于鞘糖脂聚糖的高产率和成本有效的生产,所述鞘糖脂聚糖包括含有不同唾液酸形式的那些,例如N-乙酰神经氨酸(Neu 5Ac)、N-羟乙酰神经氨酸(Neu 5Gc)、2-酮基-3-脱氧-D-甘油基-D-半乳糖基-壬酸(Kdn)和8-O-甲基-N-乙酰神经氨酸(Neu 5Ac 8 OMe)。构建了属于神经节系列、乳糖/新乳糖系列和globo/isoglobo系列鞘糖脂聚糖的64种结构不同的鞘糖脂聚糖的文库。这些聚糖是生物测定和生物医学研究的基本标准品和无价探针。
Glycosphingolipids are a diverse family of biologically important glycolipids. In addition to variations on the lipid component, more than 300 glycosphingolipid glycans have been characterized. These glycans are directly involved in various molecular recognition events. Several naturally occurring sialic acid forms have been found in sialic acid-containing glycosphingolipids, namely gangliosides. However, ganglioside glycans containing less common sialic acid forms are currently not available. Herein, highly effective one-pot multienzyme (OPME) systems are used in sequential for high-yield and cost-effective production of glycosphingolipid glycans, including those containing different sialic acid forms such as N-acetylneuraminic acid (Neu5Ac), N-glycolylneuraminic acid (Neu5Gc), 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (Kdn), and 8-O-methyl-N-acetylneuraminic acid (Neu5Ac8OMe). A library of 64 structurally distinct glycosphingolipid glycans belonging to ganglio-series, lacto-/neolacto-series, and globo-/isoglobo-series glycosphingolipid glycans is constructed. These glycans are essential standards and invaluable probes for bioassays and biomedical studies.
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