Biocatalytic preparation of N-glycolylneuraminic acid, deaminoneuraminic acid (KDN) and 9-azido-9-deoxysialic acid oligosaccharides

Biocatalytic preparation of N-glycolylneuraminic acid, deaminoneuraminic acid (KDN) and 9-azido-9-deoxysialic acid oligosaccharides
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DOI:
10.1002/adsc.200303032
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发表时间:
2003-06-01
影响因子:
5.4
通讯作者:
Paulson, JC
Paulson, JC
中科院分区:
化学2区
文献类型:
--
作者:
Blixt, O;Paulson, JC

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介绍了一种简便的制备性合成含N-羟乙酰神经氨酸、脱氨基神经氨酸和两种9-叠氮衍生物的唾液酸寡糖的方法。通过使用6-碳甘露糖/甘露糖胺前体,采用醛缩酶、CMP-唾液酸合成酶和唾液酸转移酶来完成合成。使用五种不同的唾液酸转移酶和各种受体底物的组合,合成了代表糖蛋白和糖脂中发现的序列的16种唾液酸苷,典型产率为60- 80%。
A facile approach for preparative synthesis of sialyloligosaccharides containing N-glycolylneuraminic acid, deaminoneuraminic acid, and two 9-azido derivatives is described. Synthesis is accomplished by use of 6-carbon mannose/mannosamine precursors employing an aldolase, CMP-sialic acid synthetase, and sialyltransferase. Using a combination of five different sialyltransferases and various acceptor substrates, 16 sialosides representing sequences found in glycoproteins and glycolipids were synthesized with typical yields of 60-80%.