Microwave-assisted simultaneous O,N-sulfonation in the synthesis of heparin-like oligosaccharides

doi:10.1039/c5qo00320b

	Microwave-assisted simultaneous O,N-sulfonation in the synthesis of heparin-like oligosaccharides
	Xu, Peng 1; Laval, Stephane 1; Guo, Zheng2 ; Yu, Biao1,2
	2016
发表期刊	ORGANIC CHEMISTRY FRONTIERS (IF:4.6[JCR-2023],4.3[5-Year])
ISSN	2052-4129
卷号	3 期号:1 页码:103-109
发表状态	已发表
DOI	10.1039/c5qo00320b
摘要	The synthesis of well-defined fragments of heparin (HP) and heparan sulfate (HS) is often hampered by difficult post-assembly manipulations on the fully elaborated oligosaccharides. In particular, the O- and N-sulfonation steps, usually performed separately, require long reaction times and often result in low yield due to problems associated with the incompletion of the reaction and the purification of highly sulfonated products, thus representing a bottle-neck in the synthesis. We report herein an effective micro-wave-assisted protocol for the simultaneous O, N-sulfonation of HP/HS-like saccharides. Complete O- and N-sulfonation were attained when using a SO3 center dot NEt3 complex in a solvent mixture of NEt3/pyridine at 100 degrees C (MW heating) for 15 min, thus facilitating the purification process. Easy to implement, per-O, N-sulfonation of mono-, di-, tri- and tetra-saccharides with two to six reactive sites was performed effectively in short reaction times and excellent yields (>90%). Under smooth deprotection conditions, the resulting per-O, N-sulfonated saccharides were fully deprotected in high yields (>88%), providing saccharides pertinent to the synthesis of HP/HS-like fragments, including three tetrasaccharides relevant to the substrate of heparanase. Moreover, we developed a microwave-assisted protocol for the one-pot selective O-sulfonation/N-acetylation on disaccharide 7, which could be applied to synthesize the members of the GAG family bearing N-acetyl groups.
收录类别	SCI ; EI
语种	英语
资助项目	National Natural Science Foundation of China[21432012]
WOS研究方向	Chemistry
WOS类目	Chemistry, Organic
WOS记录号	WOS:000366864700017
出版者	ROYAL SOC CHEMISTRY
EI入藏号	20184806136330
EI主题词	Bottles ; Oligosaccharides ; Polysaccharides ; Purification ; Sulfur compounds
EI分类号	Packaging Materials:694.2 ; Chemical Reactions:802.2 ; Organic Compounds:804.1
WOS关键词	SOLID-PHASE SYNTHESIS ; BIOLOGICAL EVALUATION ; BUILDING-BLOCKS ; HIGH-AFFINITY ; SULFATE ; BINDING ; SUBSTRATE ; PENTASACCHARIDE ; HEXASACCHARIDE ; ACID
原始文献类型	Article
引用统计	正在获取...
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/2062
专题	物质科学与技术学院物质科学与技术学院_特聘教授组_俞飚组物质科学与技术学院_博士生
通讯作者	Xu, Peng; Yu, Biao
作者单位	1.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China 2.ShanghaiTech Univ, Sch Phys Sci & Technol, Shanghai 201210, Peoples R China
通讯作者单位	物质科学与技术学院
推荐引用方式 GB/T 7714	Xu, Peng,Laval, Stephane,Guo, Zheng,et al. Microwave-assisted simultaneous O,N-sulfonation in the synthesis of heparin-like oligosaccharides[J]. ORGANIC CHEMISTRY FRONTIERS,2016,3(1):103-109.
APA	Xu, Peng,Laval, Stephane,Guo, Zheng,&Yu, Biao.(2016).Microwave-assisted simultaneous O,N-sulfonation in the synthesis of heparin-like oligosaccharides.ORGANIC CHEMISTRY FRONTIERS,3(1),103-109.
MLA	Xu, Peng,et al."Microwave-assisted simultaneous O,N-sulfonation in the synthesis of heparin-like oligosaccharides".ORGANIC CHEMISTRY FRONTIERS 3.1(2016):103-109.