Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
Associated disease: infection due to Cryptococcus neoformans [ICD11:
XN3EH 
]
The structure was elucidated in this paperNCBI PubMed ID: 19345342Publication DOI: 10.1016/j.carres.2009.03.003Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Heiss C <cheiss
ccrc.uga.edu>, Heiss C <heiss8
bellsouth.net>
Institutions: Analytical Services/Complex Carbohydrate Research Center—University of Georgia, Athens, GA, USA, University of Iowa Carver College of Medicine and VA Medical Center, Iowa City, Iowa, USA, Department of Molecular Microbiology, Washington University School of Medicine, St. Louis, Missouri, USA
The structure of galactoxylomannan, a capsular polysaccharide from the opportunistic yeast Cryptococcus neoformans, was re-examined by NMR spectroscopy and GC-MS. The residue that is 3-linked to the side chain galactose and was previously assigned as β-D-xylose [Vaishnav, V. V.; Bacon, B. E.; O'Neill, M.; Cherniak, R. Carbohydr. Res.1998, 306, 315-330] was determined to be β-D-glucuronic acid. A revised structure for this polymer is presented, along with a proposal that this compound be termed glucuronoxylomannogalactan (GXMGal).
structure, polysaccharides, glucuronic acid, CPS, Cryptococcus neoformans, GalXM
Structure type: polymer chemical repeating unit
Location inside paper: p.916, fig.1B, (GXMGal)
Trivial name: glucuronoxylomannogalactan (GXMGal)
Compound class: CPS
Contained glycoepitopes: IEDB_114701,IEDB_115136,IEDB_130701,IEDB_134624,IEDB_136044,IEDB_136906,IEDB_137472,IEDB_140630,IEDB_141794,IEDB_144983,IEDB_145668,IEDB_151528,IEDB_152206,IEDB_164174,IEDB_167188,IEDB_174332,IEDB_190606,IEDB_423153,IEDB_983930,SB_163,SB_165,SB_166,SB_187,SB_195,SB_197,SB_44,SB_67,SB_7,SB_72,SB_88
Methods: 13C NMR, 1H NMR, methylation, gel filtration, NMR-2D, GC-MS, sugar analysis, acid hydrolysis, GC, composition analysis, permethylation, reduction with NaBD4, acetylation
Comments, role: revised structure obtained from Cryptococcus neoformans D wild type; NMR data at D2O pD 7.4 of bDGlcpA residue, 1H: 4.70 3.37 3.53 3.56 3.68 -, 13C: 105.0 74.3 76.5 72.5 76.4 176.0.
Related record ID(s): 23710, 45073, 45074
NCBI Taxonomy refs (TaxIDs): 40410Reference(s) to other database(s): GTC:G57906UG
Show glycosyltransferases
NMR conditions: in D2O; pH 4.6 at 343 K
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6
6,3,3 30%bDGlcpA 105.1 74.0 76.4 72.7 75.7 ?
6,3,4,2 bDXylp 104.4 73.6 76.6 70.2 66.1
6,3,4,3,3 70%bDXylp 101.9 73.9 76.6 70.1 66.1
6,3,4,3 aDManp 102.6 68.6 79.1 66.0 70.5 61.5
6,3,4 aDManp 100.6 79.2 76.5 67.2 71.0 61.3
6,3 bDGalp 105.1 71.6 81.5 76.8 74.2 62.0
6 aDGalp 99.1 68.3 80.9 70.1 69.8 67.6
aDGalp 99.2 69.3 70.5 70.5 69.8 67.6
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6
6,3,3 30%bDGlcpA 4.75 3.39 3.56 3.56 3.87 -
6,3,4,2 bDXylp 4.39 3.31 3.46 3.64 3.34-4.02
6,3,4,3,3 70%bDXylp 4.54 3.39 3.49 3.68 3.32-4.02
6,3,4,3 aDManp 5.22 4.25 4.03 3.81 4.04 3.69-3.74
6,3,4 aDManp 4.99 4.12 4.07 3.87 4.08 3.84-3.86
6,3 bDGalp 4.69 3.84 3.86 4.30 3.79 3.75-3.80
6 aDGalp 5.01 4.06 4.01 4.29 4.20 3.71-3.93
aDGalp 4.98 3.85 3.89 4.04 4.20 3.71-3.93
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6
6,3,3 30%bDGlcpA 105.1/4.75 74.0/3.39 76.4/3.56 72.7/3.56 75.7/3.87
6,3,4,2 bDXylp 104.4/4.39 73.6/3.31 76.6/3.46 70.2/3.64 66.1/3.34-4.02
6,3,4,3,3 70%bDXylp 101.9/4.54 73.9/3.39 76.6/3.49 70.1/3.68 66.1/3.32-4.02
6,3,4,3 aDManp 102.6/5.22 68.6/4.25 79.1/4.03 66.0/3.81 70.5/4.04 61.5/3.69-3.74
6,3,4 aDManp 100.6/4.99 79.2/4.12 76.5/4.07 67.2/3.87 71.0/4.08 61.3/3.84-3.86
6,3 bDGalp 105.1/4.69 71.6/3.84 81.5/3.86 76.8/4.30 74.2/3.79 62.0/3.75-3.80
6 aDGalp 99.1/5.01 68.3/4.06 80.9/4.01 70.1/4.29 69.8/4.20 67.6/3.71-3.93
aDGalp 99.2/4.98 69.3/3.85 70.5/3.89 70.5/4.04 69.8/4.20 67.6/3.71-3.93
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 |
|---|
| 6,3,3 | 30%bDGlcpA | 4.75 | 3.39 | 3.56 | 3.56 | 3.87 |
|
| 6,3,4,2 | bDXylp | 4.39 | 3.31 | 3.46 | 3.64 | 3.34
4.02 | |
| 6,3,4,3,3 | 70%bDXylp | 4.54 | 3.39 | 3.49 | 3.68 | 3.32
4.02 | |
| 6,3,4,3 | aDManp | 5.22 | 4.25 | 4.03 | 3.81 | 4.04 | 3.69
3.74 |
| 6,3,4 | aDManp | 4.99 | 4.12 | 4.07 | 3.87 | 4.08 | 3.84
3.86 |
| 6,3 | bDGalp | 4.69 | 3.84 | 3.86 | 4.30 | 3.79 | 3.75
3.80 |
| 6 | aDGalp | 5.01 | 4.06 | 4.01 | 4.29 | 4.20 | 3.71
3.93 |
| | aDGalp | 4.98 | 3.85 | 3.89 | 4.04 | 4.20 | 3.71
3.93 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 |
|---|
| 6,3,3 | 30%bDGlcpA | 105.1 | 74.0 | 76.4 | 72.7 | 75.7 | ? |
| 6,3,4,2 | bDXylp | 104.4 | 73.6 | 76.6 | 70.2 | 66.1 | |
| 6,3,4,3,3 | 70%bDXylp | 101.9 | 73.9 | 76.6 | 70.1 | 66.1 | |
| 6,3,4,3 | aDManp | 102.6 | 68.6 | 79.1 | 66.0 | 70.5 | 61.5 |
| 6,3,4 | aDManp | 100.6 | 79.2 | 76.5 | 67.2 | 71.0 | 61.3 |
| 6,3 | bDGalp | 105.1 | 71.6 | 81.5 | 76.8 | 74.2 | 62.0 |
| 6 | aDGalp | 99.1 | 68.3 | 80.9 | 70.1 | 69.8 | 67.6 |
| | aDGalp | 99.2 | 69.3 | 70.5 | 70.5 | 69.8 | 67.6 |
|
![](nmr_drawer.py?width=750&height=130&nucleus=C&rotate_labels=false&spectrum=[{"s":105.1,"l":"1","c":[0,0,225]},{"s":74,"l":"2","c":[0,0,225]},{"s":76.4,"l":"3","c":[0,0,225]},{"s":72.7,"l":"4","c":[0,0,225]},{"s":75.7,"l":"5","c":[0,0,225]},{"s":104.4,"l":"1","c":[230,0,30]},{"s":73.6,"l":"2","c":[230,0,30]},{"s":76.6,"l":"3","c":[230,0,30]},{"s":70.2,"l":"4","c":[230,0,30]},{"s":66.1,"l":"5","c":[230,0,30]},{"s":101.9,"l":"1","c":[0,165,0]},{"s":73.9,"l":"2","c":[0,165,0]},{"s":76.6,"l":"3","c":[0,165,0]},{"s":70.1,"l":"4","c":[0,165,0]},{"s":66.1,"l":"5","c":[0,165,0]},{"s":102.6,"l":"1","c":[120,0,225]},{"s":68.6,"l":"2","c":[120,0,225]},{"s":79.1,"l":"3","c":[120,0,225]},{"s":66,"l":"4","c":[120,0,225]},{"s":70.5,"l":"5","c":[120,0,225]},{"s":61.5,"l":"6","c":[120,0,225]},{"s":100.6,"l":"1","c":[0,192,255]},{"s":79.2,"l":"2","c":[0,192,255]},{"s":76.5,"l":"3","c":[0,192,255]},{"s":67.2,"l":"4","c":[0,192,255]},{"s":71,"l":"5","c":[0,192,255]},{"s":61.3,"l":"6","c":[0,192,255]},{"s":105.1,"l":"1","c":[220,0,180]},{"s":71.6,"l":"2","c":[220,0,180]},{"s":81.5,"l":"3","c":[220,0,180]},{"s":76.8,"l":"4","c":[220,0,180]},{"s":74.2,"l":"5","c":[220,0,180]},{"s":62,"l":"6","c":[220,0,180]},{"s":99.1,"l":"1","c":[100,160,0]},{"s":68.3,"l":"2","c":[100,160,0]},{"s":80.9,"l":"3","c":[100,160,0]},{"s":70.1,"l":"4","c":[100,160,0]},{"s":69.8,"l":"5","c":[100,160,0]},{"s":67.6,"l":"6","c":[100,160,0]},{"s":99.2,"l":"1","c":[210,210,0]},{"s":69.3,"l":"2","c":[210,210,0]},{"s":70.5,"l":"3","c":[210,210,0]},{"s":70.5,"l":"4","c":[210,210,0]},{"s":69.8,"l":"5","c":[210,210,0]},{"s":67.6,"l":"6","c":[210,210,0]}])
The spectrum also has 1 signal at unknown position (not plotted). |
There is only one chemically distinct structure:
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Found 1 record.
Displayed record 1
(later renamed to: Cryptococcus neoformans var. neoformans (Cap67))