Isolation and identification of poly-α-(1→4)-linked 3- O-methyl- d-mannopyranose from a hot-water extract of Mycobacterium vaccae

A polysaccharide around 3.6 kDa has been identified as the major carbohydrate moiety of a antineoplastic protein–polysaccharide complex (PS4A) obtained by boiling intact cells of Mycobacterium vaccae in water. 1H and 13C NMR spectra of this polysaccharide suggested it was a highly homogeneous polyme...

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Veröffentlicht in:	Carbohydrate research 2000-01, Vol.324 (1), p.38-44
Hauptverfasser:	Tian, Xin-Xin, Li, Afeng, Farrugia, Isabelle V, Mo, Xuesheng, Crich, David, Groves, Michael J
Format:	Artikel
Sprache:	eng
Schlagworte:	Adjuvants, Immunologic - chemistry Carbohydrate Conformation Chromatography, High Pressure Liquid Magnetic Resonance Spectroscopy Mannans - chemistry Methylation Mycobacterium - chemistry Mycobacterium vaccae Poly-α-(1→4)-3- O-methyl mannopyranose Polysaccharides, Bacterial - chemistry Protein–polysaccharide complex Synthesis
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description	A polysaccharide around 3.6 kDa has been identified as the major carbohydrate moiety of a antineoplastic protein–polysaccharide complex (PS4A) obtained by boiling intact cells of Mycobacterium vaccae in water. 1H and 13C NMR spectra of this polysaccharide suggested it was a highly homogeneous polymer composed substantially of one monomer, probably an α-linked O-methylated mannose. Comparison of the COSY spectra of the original and acetylated polymer indicated that the glycosidic linkage and the methyl ether were interchangeable, at O-3 and O-4. Further study demonstrated that the benzyolated hydrolysate of the polymer was 1,2,4,6-tetra- O-benzoyl-3- O-methyl-β-mannopyranose. The hydrolysate was 3- O-methyl-α,β-mannopyranose and the polymer was therefore poly-α-(1→4)-linked 3- O-methyl- d-mannopyranose. This conclusion was further confirmed with an authentic sample of the monomer, which had spectral data identical to those of the hydrolyzate and co-eluted from an ion-exchange HPLC with the major sugar in the hydrolysate.
doi_str_mv	10.1016/S0008-6215(99)00248-7
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Comparison of the COSY spectra of the original and acetylated polymer indicated that the glycosidic linkage and the methyl ether were interchangeable, at O-3 and O-4. Further study demonstrated that the benzyolated hydrolysate of the polymer was 1,2,4,6-tetra- O-benzoyl-3- O-methyl-β-mannopyranose. The hydrolysate was 3- O-methyl-α,β-mannopyranose and the polymer was therefore poly-α-(1→4)-linked 3- O-methyl- d-mannopyranose. 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Comparison of the COSY spectra of the original and acetylated polymer indicated that the glycosidic linkage and the methyl ether were interchangeable, at O-3 and O-4. Further study demonstrated that the benzyolated hydrolysate of the polymer was 1,2,4,6-tetra- O-benzoyl-3- O-methyl-β-mannopyranose. The hydrolysate was 3- O-methyl-α,β-mannopyranose and the polymer was therefore poly-α-(1→4)-linked 3- O-methyl- d-mannopyranose. 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source	MEDLINE; ScienceDirect Journals (5 years ago - present)
subjects	Adjuvants, Immunologic - chemistry Carbohydrate Conformation Chromatography, High Pressure Liquid Magnetic Resonance Spectroscopy Mannans - chemistry Methylation Mycobacterium - chemistry Mycobacterium vaccae Poly-α-(1→4)-3- O-methyl mannopyranose Polysaccharides, Bacterial - chemistry Protein–polysaccharide complex Synthesis
title	Isolation and identification of poly-α-(1→4)-linked 3- O-methyl- d-mannopyranose from a hot-water extract of Mycobacterium vaccae
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