Microbial Physiology, Groningen Biomolecular Sciences and Biotechnology Institute (GBB) , University of Groningen , Nijenborgh 7 , 9747 AG Groningen , The Netherlands.
Eurofins Carbohydrate Competence Centre , 8440 AT Heerenveen , The Netherlands.
J Agric Food Chem. 2019 Mar 27;67(12):3469-3479. doi: 10.1021/acs.jafc.8b06974. Epub 2019 Mar 14.
Sialylated oligosaccharides contribute 12.6-21.9% of total free oligosaccharides in human milk ( hMOS). These acidic hMOS possess prebiotic properties and display antiadhesive effects against pathogenic bacteria. Only limited amounts of sialylated hMOS are currently available. The aim of our work is to enzymatically synthesize sialylated oligosaccharides mimicking hMOS functionality. In this study, we tested mixtures of glucosylated-lactose (GL34), galactosylated-lactulose (LGOS), and galacto-oligosaccharide (Vivinal GOS) molecules, as trans-sialylation acceptor substrates. The recombinant trans-sialidase enzyme from Trypanosoma cruzi (TcTS) was used for enzymatic decoration, transferring (α2→3)-linked sialic acid from donor substrates to nonreducing terminal β-galactopyranosyl units of these acceptor substrates. The GL34 F2 2-Glc-Lac compound with an accessible terminal galactosyl residue was sialylated efficiently (conversion degree of 47.6%). TcTS sialylated at least 5 LGOS structures and 11 Vivinal GOS DP3-4 compounds. The newly synthesized sialylated oligosaccharides are interesting as potential hMOS mimics for applications in biomedical and functional-food products.
唾液酸化低聚糖占人乳中总游离低聚糖的 12.6-21.9%（hMOS）。这些酸性 hMOS 具有益生元特性，并对病原菌表现出抗黏附作用。目前可获得的唾液酸化 hMOS 数量有限。我们的工作旨在通过酶法合成模拟 hMOS 功能的唾液酸化低聚糖。在这项研究中，我们测试了葡萄糖基乳糖（GL34）、半乳糖基乳果糖（LGOS）和半乳糖低聚糖（Vivinal GOS）混合物作为转涎酸作用的接受底物。我们使用来自克氏锥虫（TcTS）的重组转涎酸酶作为酶促修饰，将（α2→3）-连接的唾液酸从供体底物转移到这些接受底物的非还原末端β-半乳糖吡喃基单元上。具有可及末端半乳糖残基的 GL34 F2 2-Glc-Lac 化合物能够有效地被唾液酸化（转化率为 47.6%）。TcTS 至少对 5 个 LGOS 结构和 11 个 Vivinal GOS DP3-4 化合物进行了唾液酸化。新合成的唾液酸化低聚糖作为潜在的 hMOS 模拟物，可用于生物医学和功能性食品产品。
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