Further characterization of allergenically active oligosaccharitols isolated from a sea squirt H-antigen.
Complete primary structures of five allergenically active oligosaccharitols (HPG-beta 2-N5a, -N6, -N7a, -N7b, and -N9) derived from a sea squirt H-antigen were studied. Structural characterization was carried out by a new method in which products of limited periodate oxidation, followed by derivatization with p-aminobenzoic acid ethyl ester, were analyzed by a combination of HPLC, fast atom-bombardment mass spectrometry, sequential glycosidase digestion, methylation analysis, and 500-MHz 1H NMR. Established structures of GalNAc beta 1-4 (GalNAc alpha 1-2Fuc alpha 1-3) GlcNAc beta 1-3GalNAc-ol, GalNAc beta 1-4GlcNAc beta 1-3 (GalNAc beta 1-4GlcNAc beta 1-6) GalNAc-ol, GalNAc beta 1-4GlcNAc beta 1-3[GalNAc beta 1-4 (Fuc alpha 1-3) GlcNAc beta 1-6] GalNAc-ol, GalNAc beta 1-4 (Fuc alpha 1-3) GlcNAc beta 1-3[GalNAc beta 1-4 (Fuc alpha 1-3) GlcNAc beta 1-6] GalNAc-ol, and GalNAc beta 1-4 (GalNAc alpha 1-2Fuc alpha 1-3)GlcNAc beta 1-3 [GalNAc beta 1-4 (GalNAc alpha 1-2Fuc alpha 1-3)GlcNAc beta 1-6]GalNAc-ol are represented by HPG-beta 2-N5a, -N6, -N7a, -N7b, and -N9, respectively. These structures have not been encountered previously. Oligosaccharide units GalNAc alpha 1-2Fuc alpha 1-, GalNAc beta 1-4GlcNAc beta 1-, and Fuc alpha 1-3GlcNAc beta 1- are considered to be the allergenically specific epitopes. Partial assignments of 500-MHz 1H NMR spectra of these novel O-linked oligosaccharitols were attempted.
Ohta
M
M
Department of Biotechnology, Faculty of Engineering, Fukuyama University, Hiroshima, Japan.
Matsuura
F
F
Kobayashi
Y
Y
Shigeta
S
S
Ono
K
K
Oka
S
S
D000485:Allergens / Q000009:adverse effects / Q000737:chemistry* / Q000302:isolation & purification; D000818:Animals; D001566:Benzocaine; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006023:Glycoproteins / Q000276:immunology*; D006026:Glycoside Hydrolases / Q000737:chemistry; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry* / Q000276:immunology / Q000302:isolation & purification; D010084:Oxidation-Reduction; D010504:Periodic Acid / Q000737:chemistry; D014561:Urochordata / Q000737:chemistry / Q000276:immunology*
D000485:Allergens; C053192:Gi-rep antigen, Sea squirt; D006023:Glycoproteins; D009844:Oligosaccharides; D010504:Periodic Acid; C009288:metaperiodate; D006026:Glycoside Hydrolases; D001566:Benzocaine