Bulletin of the Korean Chemical Society

  • 제30권11호
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  • Pages.2535-2541
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  • 2009
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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A Systematic NMR Determination of α-D-Glucooligosaccharides, Effect of Linkage Type, Anomeric Configuration and Combination of Different Linkages Type on 13C Chemical Shifts for the Determination of Unknown Isomaltooligosaccharides

  • Goffin, Dorothee (Unité de Chimie Biologique Industrielle, Unité de Technologie des Industries Agro-alimentaires) ;
  • Bystricky, Peter (Centre for BioAnalytical Sciences, Department of Chemistry, National University of Ireland, Galway, University Road) ;
  • Shashkov, Alexander S. (N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences) ;
  • Lynch, Mary (Centre for BioAnalytical Sciences, Department of Chemistry, National University of Ireland, Galway, University Road) ;
  • Hanon, Emilien (Faculté Universitaire des Sciences Agronomiques de Gembloux, Unité de Chimie Générale et Organique) ;
  • Paquot, Michel (Faculté Universitaire des Sciences Agronomiques de Gembloux, Unité de Chimie Biologique Industrielle) ;
  • Savage, Angela V. (Centre for BioAnalytical Sciences, Department of Chemistry, National University of Ireland, Galway, University Road)
  • 발행 : 2009.11.20
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초록

Prebiotic isomaltooligosaccharide preparations contain $\alpha$-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 $\sim$10), linkages types and positions (IMOs: $\alpha$-(1$\rightarrow$2, 3, 6 and in a lower proportion internal 1$\rightarrow$4) linkages, MOs: α-(1$\rightarrow$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 $^{13}C$ 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, $^{13}C$ NMR, APT and ${^1}H-{^1}H$ COSY, TOCSY, NOESY and <$^1H-{^{13}}C$ 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 $^{13}C$ specific spectral features can be identified as tools for structural analysis of isomaltooligosaccharides.

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