Hydroxyl groups introducing NMR strategy for structural elucidation of a heptasaccharide isolated from Trillium tschonoskii.

IF 2.4 3区化学 Q3 BIOCHEMISTRY & MOLECULAR BIOLOGY

Carbohydrate Research Pub Date : 2024-12-17 DOI:10.1016/j.carres.2024.109359

Juan Song, Guangzhong Tu, Yue Liu, Si Liu, Yuting Zhang, Wenxi Yang, Xu Pang, Xiaojuan Chen, Haizhen Liang, Jie Zhang, Baiping Ma

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引用次数: 0

Abstract

A heptasaccharide was isolated from an active fraction of Trillium tschonoskii using HILIC and high-temperature PGC chromatography methods. UHPLC-Q/TOF-MS analysis gave this oligosaccharide a degree of polymerization (DP) of 7 and MS/MS showed that it has a six-carbon aldehyde glucan structure with the possible chain 1 → 4 connected. The structure was determined by series 1D and 2D NMR in two solvents D₂O and DMSO‑d₆. Using ¹H resonances of the -OH groups as the starting point and HSQC-TOCSY on the covalent structure definition for structural elucidation allowed this heptasaccharide to be uncovered. This heptasaccharide was elucidated as maltoheptaose via complete assignment of ¹H and ¹³C with jigsaw H-C-OH pieces produced by HSQC-TOCSY at increasing mixing time. The significance of identifying maltoheptaose in Trillium tschonoskii indicates the high potential of -OH introducing strategy for other oligosaccharides' structural determination with relatively higher DP.

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来源期刊

Carbohydrate Research 化学-生化与分子生物学

CiteScore

5.00

自引率

3.20%

发文量

183

审稿时长

3.6 weeks

期刊介绍： Carbohydrate Research publishes reports of original research in the following areas of carbohydrate science: action of enzymes, analytical chemistry, biochemistry (biosynthesis, degradation, structural and functional biochemistry, conformation, molecular recognition, enzyme mechanisms, carbohydrate-processing enzymes, including glycosidases and glycosyltransferases), chemical synthesis, isolation of natural products, physicochemical studies, reactions and their mechanisms, the study of structures and stereochemistry, and technological aspects. Papers on polysaccharides should have a "molecular" component; that is a paper on new or modified polysaccharides should include structural information and characterization in addition to the usual studies of rheological properties and the like. A paper on a new, naturally occurring polysaccharide should include structural information, defining monosaccharide components and linkage sequence. Papers devoted wholly or partly to X-ray crystallographic studies, or to computational aspects (molecular mechanics or molecular orbital calculations, simulations via molecular dynamics), will be considered if they meet certain criteria. For computational papers the requirements are that the methods used be specified in sufficient detail to permit replication of the results, and that the conclusions be shown to have relevance to experimental observations - the authors'' own data or data from the literature. Specific directions for the presentation of X-ray data are given below under Results and "discussion".