NMR characterization of endogenously O-acetylated oligosaccharides isolated from tomato (Lycopersicon esculentum) xyloglucan

作者: Zhonghua Jia , Michael Cash , Alan G. Darvill , William S. York

DOI: 10.1016/J.CARRES.2005.04.015

关键词: NMR spectra databaseAcetylationGlycanChemistryStereochemistryPolysaccharideBiochemistryResidue (chemistry)OligosaccharideNuclear magnetic resonance spectroscopyXyloglucanOrganic chemistryAnalytical chemistryGeneral Medicine

摘要: Abstract Eight oligosaccharide subunits, generated by endoglucanase treatment of the plant polysaccharide xyloglucan isolated from culture filtrate suspension-cultured tomato ( Lycopersicon esculentum ) cells, were structurally characterized NMR spectroscopy. These oligosaccharides, which contain up to three endogenous O -acetyl substituents, consist a cellotetraose core with α- d -Xyl p residues at O-6 two β- -Glc non-reducing end core. Some themselves bear either an l -Ara or -Gal residue O-2. -Acetyl substituents are located unbranched (internal) residue, terminal and/or O-5 residue. Structural assignments facilitated long-range scalar coupling interactions observed in high-resolution gCOSY spectra oligosaccharides. The presence five-bond constants provides direct method assigning O-acetylation sites, may prove generally useful analysis O-acylated glycans. Spectral assignment these endogenously O-acetylated oligosaccharides makes it possible deduce correlations between their structural features and chemical shifts diagnostic resonances spectra.

参考文章(23)
Robert M. K. Carlson, William R. Croasmun, Two-dimensional NMR spectroscopy: applications for chemists and biochemists. VCH Publishers , VCH Verlagsgesellschaft. ,(1987)
Pieter A. Roelofsen, The plant cell-wall Gebrüder Borntraeger. ,(1959)
Johannes F.G. Vliegenthart, Lambertus Dorland, Herman van Halbeek, High-Resolution, 1H-Nuclear Magnetic Resonance Spectroscopy as a Tool in the Structural Analysis of Carbohydrates Related to Glycoproteins Advances in Carbohydrate Chemistry and Biochemistry. ,vol. 41, pp. 209- 374 ,(1983) , 10.1016/S0065-2318(08)60059-1
Juan Carlos Cobas, F. Javier Sardina, Nuclear magnetic resonance data processing. MestRe‐C: A software package for desktop computers Concepts in Magnetic Resonance Part A. ,vol. 19, pp. 80- 96 ,(2003) , 10.1002/CMR.A.10089
William S. York, Giuseppe Impallomeni, Makoto Hisamatsu, Peter Albersheim, Alan G. Darvill, ELEVEN NEWLY CHARACTERIZED XYLOGLUCAN OLIGOGLYCOSYL ALDITOLS : THE SPECIFIC EFFECTS OF SIDECHAIN STRUCTURE AND LOCATION ON 1H NMR CHEMICAL SHIFTS Carbohydrate Research. ,vol. 267, pp. 79- 104 ,(1995) , 10.1016/0008-6215(94)00287-P
William S. York, V.S. Kumar Kolli, Ron Orlando, Peter Albersheim, Alan G. Darvill, The structures of arabinoxyloglucans produced by solanaceous plants. Carbohydrate Research. ,vol. 285, pp. 99- 128 ,(1996) , 10.1016/S0008-6215(96)90176-7
Barbara S. Valent, Peter Albersheim, The Structure of Plant Cell Walls Plant Physiology. ,vol. 54, pp. 105- 108 ,(1974) , 10.1104/PP.54.1.105
Zhonghua Jia, Qiang Qin, Alan G. Darvill, William S. York, Structure of the xyloglucan produced by suspension-cultured tomato cells. Carbohydrate Research. ,vol. 338, pp. 1197- 1208 ,(2003) , 10.1016/S0008-6215(03)00079-X
Stephen C. Fry, William S. York, Peter Albersheim, Alan Darvill, Takahisa Hayashi, Jean-Paul Joseleau, Yoji Kato, Ester Perez Lorences, Gordon A. Maclachlan, Michael McNeil, Andrew J. Mort, J. S. Grant Reid, Hanns Ulrich Seitz, Robert R. Selvendran, Alphons G. J. Voragen, Alan R. White, An unambiguous nomenclature for xyloglucan‐derived oligosaccharides Physiologia Plantarum. ,vol. 89, pp. 1- 3 ,(1993) , 10.1111/J.1399-3054.1993.TB01778.X
William S. York, Herman van Halbeek, Alan G. Darvill, Peter Albersheim, Structural analysis of xyloglucan oligosaccharides by 1H-n.m.r. spectroscopy and fast-atom-bombardment mass spectrometry. Carbohydrate Research. ,vol. 200, pp. 9- 31 ,(1990) , 10.1016/0008-6215(90)84179-X