Glycohub, Inc. , 4070 Truxel Road, Sacramento, California 95834, United States.
Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.
J Org Chem. 2016 Nov 18;81(22):10809-10824. doi: 10.1021/acs.joc.6b01905. Epub 2016 Oct 24.
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.
糖脂是一类具有重要生物学意义的糖脂。除了脂质成分的变化外，已经有 300 多种糖脂聚糖被鉴定出来。这些聚糖直接参与各种分子识别事件。在含有唾液酸的糖脂中，如神经节苷脂中，已经发现了几种天然存在的唾液酸形式。然而，目前还没有含有较少见的唾液酸形式的神经节苷脂聚糖。在此，我们使用高效的一锅多酶（OPME）系统进行连续酶解反应，以高产率和高性价比地生产糖脂聚糖，包括含有不同唾液酸形式的聚糖，如 N-乙酰神经氨酸（Neu5Ac）、N-羟乙酰神经氨酸（Neu5Gc）、2-酮基-3-脱氧-d-甘油-d-半乳糖壬酮酸（Kdn）和 8-O-甲基-N-乙酰神经氨酸（Neu5Ac8OMe）。构建了一个包含 64 种结构不同的糖脂聚糖的文库，这些糖脂聚糖属于神经节苷脂、乳/新乳苷脂和Globoside/Isogloboside 糖脂聚糖系列。这些聚糖是生物测定和生物医学研究中必不可少的标准品和非常有价值的探针。
