迈向硫酸乙酰肝素寡糖的化学酶法合成：用铈铵盐氧化裂解对硝基苯基基团。
Towards the chemoenzymatic synthesis of heparan sulfate oligosaccharides: Oxidative cleavage of -nitrophenyl group with ceric ammonium salts.
作者信息
Cai Chao, Li Lingyun, Harvey Cate, Liu Jian, Linhardt Robert J
机构信息
Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, NY 12180, USA.
出版信息
Tetrahedron Lett. 2013 Aug 14;54(33):4471-4474. doi: 10.1016/j.tetlet.2013.06.044.
Abstract
We have developed an efficient chemoenzymatic synthesis of heparan sulfate oligosaccharides employing the -nitrophenyl (-NP) β-glucuronide as an acceptor compatible with enzymatic elongation and one that significantly simplifies oligosaccharide purification on C-18 resin. Employing ceric ammonium nitrate as oxidative reagent to remove the -NP group unexpectedly also removed the glucuronic acid residue at the reducing-end, affording a smaller oligosaccharide. The application of ceric ammonium sulfate allowed the removal of the -NP without concomitant loss of the adjacent glucuronic acid offering a route to longer heparin sulfate oligosaccharide products.
摘要
我们已经开发出一种高效的化学酶促合成硫酸乙酰肝素寡糖的方法，该方法采用对硝基苯基（-NP）β-葡萄糖醛酸苷作为与酶促延伸兼容的受体，并且能显著简化在C-18树脂上的寡糖纯化过程。意外的是，使用硝酸铈铵作为氧化试剂去除-NP基团时，也去除了还原端的葡萄糖醛酸残基，从而得到了更小的寡糖。而硫酸铈铵的应用则能够去除-NP，同时不会导致相邻葡萄糖醛酸的损失，为获得更长的硫酸乙酰肝素寡糖产物提供了一条途径。
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Glycobiology. 2013 Jul;23(7):764-77. doi: 10.1093/glycob/cwt016. Epub 2013 Mar 11.
2
Chemoenzymatic synthesis of the next generation of ultralow MW heparin therapeutics.下一代超低分子量肝素治疗药物的酶法化学合成。
Future Med Chem. 2012 Mar;4(3):289-96. doi: 10.4155/fmc.11.185.
3
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Curr Opin Pharmacol. 2012 Apr;12(2):217-9. doi: 10.1016/j.coph.2011.12.002. Epub 2012 Feb 8.
4
Chemoenzymatic synthesis of uridine diphosphate-GlcNAc and uridine diphosphate-GalNAc analogs for the preparation of unnatural glycosaminoglycans.酶促化学合成尿苷二磷酸-N-乙酰葡糖胺和尿苷二磷酸-N-乙酰半乳糖胺类似物用于制备非天然糖胺聚糖。
J Org Chem. 2012 Feb 3;77(3):1449-56. doi: 10.1021/jo202322k. Epub 2012 Jan 12.
5
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Carbohydr Polym. 2012 Jan 4;87(1):822-829. doi: 10.1016/j.carbpol.2011.08.075.
6
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