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参与PSGL-1与P-选择素相互作用的粘蛋白型唾液酸化路易斯x表位的完全酶促合成。

Complete enzymic synthesis of the mucin-type sialyl Lewis x epitope, involved in the interaction between PSGL-1 and P-selectin.

作者信息

Zeng S, Gallego R G, Dinter A, Malissard M, Kamerling J P, Vliegenthart J F, Berger E G

机构信息

Physiologisches Institut, Universität Zürich, Switzerland.

出版信息

Glycoconj J. 1999 Sep;16(9):487-97. doi: 10.1023/a:1007065803554.

DOI:10.1023/a:1007065803554
PMID:10815985
Abstract

Sialyl Lewis x (sLe(x)) is an established selectin ligand occurring on N- and O-linked glycans. Using a completely enzymic approach starting from p-nitrophenyl N-acetyl-alpha-D-galactosaminide (GalNAc(alpha1-pNp as core substrate, the sLe(x)-oligosaccharide Neu5Ac(alpha2-3)Gal(beta1-4)[Fuc(alpha1-3)]GlcNAc(beta1-6)[Gal(bet a1-3)]GalNAc(alpha1-pNp, representing the O-linked form, was synthesized in an overall yield of 32%. In a first step, Gal(beta1-3)GalNAc(alpha1-pNp was prepared in a yield of 52% using UDP-Gal and an enriched preparation of beta3-galactosyltransferase (EC 2.4.1.122) from rat liver. UDP-GlcNAc and a recombinant affinity-purified preparation of core 2 beta6-N-acetylglucosaminyltransferase (EC 2.4.1.102) fused to Protein A were used to branch the core 1 structure, affording GlcNAc(beta1-6)[Gal(beta1-3)]GalNAc(alpha1-pNp in a yield of >85%. The core 2 structure was galactosylated using UDP-Gal and purified human milk beta4-galactosyltransferase 1 (EC 2.4.1.38) (yield of >85%), then sialylated using CMP-Neu5Ac and purified recombinant alpha3-sialyltransferase 3 (EC 2.4.99.X) (yield of 87%), and finally fucosylated using GDP-Fuc and recombinant human alpha3-fucosyltransferase 6 (EC 2.4.1.152) produced in Pichia pastoris (yield of 100%). Overall 1.5 micromol of product was prepared. MALDI TOF mass spectra, and 1D and 2D TOCSY and ROESY 1H NMR analysis confirmed the obtained structure.

摘要

唾液酸化路易斯x（sLe(x)）是一种存在于N-和O-连接聚糖上的已知选择素配体。以对硝基苯基N-乙酰-α-D-半乳糖胺（GalNAc(α1-pNp)）为核心底物，采用完全酶促方法，合成了代表O-连接形式的sLe(x)寡糖Neu5Ac(α2-3)Gal(β1-4)[Fuc(α1-3)]GlcNAc(β1-6)[Gal(β1-3)]GalNAc(α1-pNp)，总产率为32%。第一步，使用UDP-Gal和大鼠肝脏中富集的β3-半乳糖基转移酶（EC 2.4.1.122）制备Gal(β1-3)GalNAc(α1-pNp)，产率为52%。使用UDP-GlcNAc和与蛋白A融合的核心2 β6-N-乙酰葡糖胺基转移酶（EC 2.4.1.102）的重组亲和纯化制剂对核心1结构进行分支，得到GlcNAc(β1-6)[Gal(β1-3)]GalNAc(α1-pNp)，产率>85%。使用UDP-Gal和纯化的人乳β4-半乳糖基转移酶1（EC 2.4.1.38）对核心2结构进行半乳糖基化（产率>85%），然后使用CMP-Neu5Ac和纯化的重组α3-唾液酸转移酶3（EC 2.4.99.X）进行唾液酸化（产率87%），最后使用GDP-Fuc和在毕赤酵母中产生的重组人α3-岩藻糖基转移酶6（EC

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