Chemoenzymatic Total Synthesis of GM3 Gangliosides Containing Different Sialic Acid Forms and Various Fatty Acyl Chains.
Chemoenzymatic Total Synthesis of GM3 Gangliosides Containing Different Sialic Acid Forms and Various Fatty Acyl Chains.
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DOI：
10.1021/acs.joc.1c00450
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发表时间：
2021-07-02
影响因子：
3.6
通讯作者：
Chen, Xi
中科院分区：
文献类型：
--
作者：
Yu, Hai;Gadi, Madhusudhan Reddy;Bai, Yuanyuan;Zhang, Libo;Li, Lei;Yin, Jun;Wang, Peng G.;Chen, Xi
神经节苷脂是一种含有唾液酸的鞘糖脂，存在于所有脊椎动物的细胞膜中。其重要的生物学功能由聚糖和神经酰胺脂质组分贡献。GM 3是一种主要的神经节苷脂，也是许多其他更复杂的神经节苷脂的前体。为了以低成本获得含有各种唾液酸形式和不同脂肪酰基链的结构多样的GM 3神经节苷脂，开发了一种改进的方法来从廉价的L-丝氨酸衍生物化学合成乳糖基鞘氨醇。然后，它被用来获得GM 3鞘氨醇从不同的修饰的唾液酸前体通过一锅多酶唾液酸化系统含有多杀性巴氏杆菌唾液酸转移酶3（PmST 3）与原位生成的糖核苷酸。然后使用高效的化学酰化和简易的C18柱纯化过程来安装不同长度和不同修饰的脂肪酰基链。化学酶法代表了一种强大的全合成策略，可以访问结构确定的GM 3神经节苷脂库以探索其功能。
Gangliosides are sialic acid-containing glycosphingolipids that have been found in the cell membranes of all vertebrates. Their important biological functions are contributed by both the glycan and the ceramide lipid components. GM3 is a major ganglioside and a precursor for many other more complex gangliosides. To obtain structurally diverse GM3 gangliosides containing various sialic acid forms and different fatty acyl chains in low cost, an improved process was developed to chemically synthesize lactosyl sphingosine from an inexpensive L-serine derivative. It was then used to obtain GM3 sphingosines from diverse modified sialic acid precursors by an efficient one-pot multienzyme sialylation system containing Pasteurella multocida sialyltransferase 3 (PmST3) with in situ generation of sugar nucleotides. A highly effective chemical acylation and facile C18-cartridge purification process was then used to install fatty acyl chains of varying lengths and different modifications. The chemoenzymatic method represents a powerful total synthetic strategy to access a library of structurally defined GM3 gangliosides to explore their functions.
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影响因子：
18.2
作者：
Geissner A;Baumann L;Morley TJ;Wong AKO;Sim L;Rich JR;So PPL;Dullaghan EM;Lessard E;Iqbal U;Moreno M;Wakarchuk WW;Withers SG
通讯作者：
Withers SG
DOI：
10.1016/j.bbaexp.2006.07.001
发表时间：
2006-07-01
期刊：
BIOCHIMICA ET BIOPHYSICA ACTA-GENE STRUCTURE AND EXPRESSION
影响因子：
--
作者：
Berselli, Patrizia;Zava, Stefania;Colombo, Irma
通讯作者：
Colombo, Irma
影响因子：
5.7
作者：
Hayashi, Nobuyoshi;Chiba, Hirofumi;Takahashi, Hiroki
通讯作者：
Takahashi, Hiroki
DOI：
10.1016/bs.pmbts.2017.12.006
发表时间：
2018
影响因子：
--
作者：
Dam DHM;Paller AS
通讯作者：
Paller AS
影响因子：
--
作者：
Bond MR;Whitman CM;Kohler JJ
通讯作者：
Kohler JJ