A Systematic NMR Determination of ¥á-D-Glucooligosaccharides, Effect of Linkage Type, Anomeric Configuration and Combination of Different Linkages Type on 13C Chemical Shifts for the Determination of Unknown Isomaltooligosaccharides

Bulletin of the Korean chemical society

Michel Paquot¹  Alexander S Shashkov¹  Emilien Hanon¹  Dorothee Goffin¹  Angela V Savage¹  Peter Bystricky¹  Mary Lynch¹ 

关键词: Isomaltooligosaccharides;    13C NMR;    Glycosylation effect;    Effect of anomeric configuration;    2D NMR;   

DOI  :  

学科分类：化学（综合）

来源: Korean Chemical Society

【 摘 要 】

Prebiotic isomaltooligosaccharide preparations contain �?-D-glucooligosaccharides comprising isomaltooligosaccharides (IMOs) and non-prebiotic maltooligosaccharides (MOs). They are both glucose oligosaccharides characterized by their degree of polymerization (DP) value (from 2 to ~10), linkages types and positions (IMOs: �?-(1�?2, 3, 6 and in a lower proportion internal 1�?4) linkages, MOs: �?-(1�?4) linkages). Their structure is the key factor for their prebiotic potential. In order to determine and elucidate the exact structure of unknown IMOs and MOs, unambiguous assignments of ¹³C and 1H chemical shifts of commercial standards, representative of IMOs and MOs diversity, have been determined using optimized standard one and two-dimensional experiments such as 1H NMR, ¹³C NMR, APT and 1H-1H COSY, TOCSY, NOESY and 1H-¹³C heteronuclear HSQC, HSQC-TOCSY, and HMBC. Here we point out the differential effect of substitution by a glucose residue at different positions on chemical shifts of anomeric as well as ring carbons together with the effect of the reducing end configuration for low DP oligosaccharides and diasteroisotopic effect for H-6 protons. From this study, structural ¹³C specific spectral features can be identified as tools for structural analysis of isomaltooligosaccharides.

【 授权许可】

Unknown