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Taxonomic group: fungi / Basidiomycota (Phylum: Basidiomycota)
Organ / tissue: capsule
Associated disease: infection due to Cryptococcus neoformans [ICD11: XN3EH

]

The structure was elucidated in this paper
Publication DOI: 10.1002/mrc.1260290808
Journal NLM ID: 9882600
Publisher: Wiley Heyden
Institutions: Complex Carbohydrate Research Center, Department of Biochemistry, The University of Georgia, Athens, USA, Department of Chemistry, Georgia State University, Atlanta, USA, Complex Carbohydrate Research Center, Department of Chemistry, The University of Georgia, Athens, USA

The primary structure of the de-O-acetylated glucuronoxylomannan isolated from Cryptococcus neoformans serotype D was characterized de novo by NMR spectroscopy. Assignment of the 1H and 13C spectra of the polysaccharide involved a combination of NMR-2D experiments including double-quantum-filtered {1H,1H} COSY, {1H,1H} TOCSY and 1H-detected {1H,13C} heteronuclear multiple quantum coherence spectroscopy. The sequence of the glycosyl residues, including the linkage positions, was deduced by {1H,1H} rotating-frame NOE (ROESY) spectroscopy. The serotype-D glucuronoxylomannan was found to be a branched polymer with a repeating pentasaccharide unit of the following structure.

carbohydrates, HMQC, TOCSY, ROESY, Cryptococcus neoformans, Glucuronoxylomannan, NMR-2D

Structure type: suggested polymer biological repeating unit ; 115000
Location inside paper: fig.2, GXM, table 1
Compound class: O-polysaccharide, glucuronoxylomannan
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_115576,IEDB_130701,IEDB_140116,IEDB_140630,IEDB_144983,IEDB_145668,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_423153,IEDB_76933,IEDB_983930,SB_197,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, deacetylation, NMR-2D, GC-MS, ion-exchange chromatography, extraction, CC
Comments, role: the published 13C NMR spectrum in DSS was shifted 1.6 ppm upfield by CSDB staff to accord to a TMS reference

Related record ID(s): 178, 40728, 40734, 43806, 43821, 44119, 50826
NCBI Taxonomy refs (TaxIDs): 40410
Reference(s) to other database(s): GTC:G53406VG
Show glycosyltransferases

NMR conditions: in DSS / 90%D2O / 10%(CD3)2CO at 330 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,2	bDGlcpA	102.66	73.63	76.46	72.55	77.70	176.23
3,3	aDManp	100.96	78.19	78.19	67.03	74.24	61.49
3	aDManp	102.94	70.71	79.71	67.19	74.24	62.12
2	bDXylp	104.07	73.68	76.57	70.20	66.04
	aDManp	101.83	78.80	76.98	68.06	74.32	61.49


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,2	bDGlcpA	4.490	3.391	3.491	3.583	3.65	-
3,3	aDManp	5.236	4.30	4.11	3.85	4.03	3.8-3.9
3	aDManp	5.198	4.235	3.99	3.87	4.00	3.8-3.9
2	bDXylp	4.387	3.322	3.429	3.66	3.27-4.02
	aDManp	5.198	4.235	4.07	3.70	3.85	3.79-3.85


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3,3,2	bDGlcpA	102.66/4.490	73.63/3.391	76.46/3.491	72.55/3.583	77.70/3.65	
3,3	aDManp	100.96/5.236	78.19/4.30	78.19/4.11	67.03/3.85	74.24/4.03	61.49/3.8-3.9
3	aDManp	102.94/5.198	70.71/4.235	79.71/3.99	67.19/3.87	74.24/4.00	62.12/3.8-3.9
2	bDXylp	104.07/4.387	73.68/3.322	76.57/3.429	70.20/3.66	66.04/3.27-4.02
	aDManp	101.83/5.198	78.80/4.235	76.98/4.07	68.06/3.70	74.32/3.85	61.49/3.79-3.85

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
3,3,2	bDGlcpA	4.490	3.391	3.491	3.583	3.65
3,3	aDManp	5.236	4.30	4.11	3.85	4.03	3.8 3.9
3	aDManp	5.198	4.235	3.99	3.87	4.00	3.8 3.9
2	bDXylp	4.387	3.322	3.429	3.66	3.27 4.02
	aDManp	5.198	4.235	4.07	3.70	3.85	3.79 3.85

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
3,3,2	bDGlcpA	102.66	73.63	76.46	72.55	77.70	176.23
3,3	aDManp	100.96	78.19	78.19	67.03	74.24	61.49
3	aDManp	102.94	70.71	79.71	67.19	74.24	62.12
2	bDXylp	104.07	73.68	76.57	70.20	66.04
	aDManp	101.83	78.80	76.98	68.06	74.32	61.49

There is only one chemically distinct structure:

*O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O[C@@H]2[C@H](O)[C@@H](O[C@H]3[C@H](O)[C@@H](CO)O[C@H](*)[C@H]3O[C@@H]3OC[C@@H](O)[C@H](O)[C@H]3O)O[C@H](CO)[C@H]2O)[C@H]1O[C@@H]1O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize