Characterization of di- and monosulfated, unsaturated heparin disaccharides with terminal N-sulfated 1,6-anhydro-beta-D-glucosamine or N-sulfated 1,6-anhydro-beta-D-mannosamine residues.
Modified heparin disaccharides were obtained by the alkaline treatment of a solution containing the disulfated heparin disaccharide DeltaHexA-alpha-(1-->4)-D-GlcNSO(3),6SO(3). Their structures were characterized by one- and two-dimensional NMR spectroscopy: DeltaHexA-alpha-(1-->4)-1,6-anhydro-GlcNSO(3), DeltaHexA-alpha-(1-->4)-1,6-anhydro-ManNSO(3) and DeltaHexA-alpha-(1-->4)-ManNSO(3),6OSO(3). NMR spectroscopy, in combination with HPLC, provided the composition of the mixture. Characteristic NMR signals of the disaccharides were identified, even at low levels, in a high field of (1)H-(13)C correlation NMR spectra (HSQC) of a low molecular weight heparin (LMWH) obtained by beta-elimination (alkaline hydrolysis) of heparin benzyl ester, providing a more complete structural profile of this class of compounds.
Mascellani
Giuseppe
G
Opocrin S.p.A., via Pacinotti 3, 41040 Corlo di Formigine, Modena, Italy. s.dazzi@opocrin.it
Guerrini
Marco
M
Torri
Giangiacomo
G
Liverani
Lino
L
Spelta
Franco
F
Bianchini
Pietro
P
D002236:Carbohydrate Conformation; D002851:Chromatography, High Pressure Liquid; D004187:Disaccharides / Q000737:chemistry*; D006493:Heparin / Q000031:analogs & derivatives* / Q000737:chemistry; D006495:Heparin, Low-Molecular-Weight / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009844:Oligosaccharides / Q000737:chemistry*; D013431:Sulfates / Q000737:chemistry*
D004187:Disaccharides; D006495:Heparin, Low-Molecular-Weight; D009844:Oligosaccharides; D013431:Sulfates; C464536:heparin disaccharide; D006493:Heparin