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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Host organism: Homo sapiens
Organ / tissue: mycelium
Associated disease: eumycetoma [ICD11: 1F29

]; infection due to Pseudallescheria boydii [ICD11: XN6BV

]

The structure was elucidated in this paper
NCBI PubMed ID: 15932920
Publication DOI: 10.1093/glycob/cwi084
Journal NLM ID: 9104124
Publisher: IRL Press at Oxford University Press
Correspondence: eliana.bergter

micro.ufrj.br
Institutions: Laboratory for Molecular Structure, National Institute for Biological Standards and Control, South Mimms, UK, Departamento de Bioquímica e Biologia Molecular, Universidade Federal do Paraná, Curitiba, Brazil, Instituto de Microbiologia, Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brazil, Faculty of Medicine, Kennedy Institute of Rheumatology Division,Imperial College London, London, UK, Faculty of Medicine, Kennedy Institute, Imperial College London, London, UK, Laboratory for Molecular Structure, National Institute for Biological Standards and Control, Hertfordshire, UK

Nonreducing O-linked oligosaccharides were obtained from the peptidorhamnomannan of mycelia of Pseudallescheria boydii by alkaline β-elimination under reducing conditions. They were separated by GPC chromatography to give three oligosaccharide fractions. The major oligosaccharide from fraction 1 was characterized by a combination of techniques including electrospray ionization quadrupole time-of-flight tandem mass spectrometry (ESI MS/MS), matrix-assisted laser desorption ionization mass spectrometry (MALDI MS), nuclear magnetic resonance (NMR), and methylation gas-liquid chromatography-mass spectrometry (GC-MS) analysis. It was branched, with a principal chain of α-Rhap-(1→3)-α-Rhap-(1→3)-α-Manp-(1→2)-Man-ol substituted at O-6 of mannitol with an α-Glcp-(1→4)-β-Galp group. Species containing one and two additional α-Glcp-(1→4) substituents in the rhamnose branch were also present. The major component of fraction 2 was a substructure of oligosaccharide-1, lacking a hexose from the Glc-Gal branch. Fraction 3 contained a mixture of smaller, unbranched, oligosaccharides. In hapten inhibition tests, fractions 1 and 2 blocked the reaction between peptidorhamnomannan (PRM) and rabbit anti-P. boydii mycelium hyperimmune serum by ~75%, whereas fraction 3 inhibited by ~55%.

ESI MS, ELISA, mycelia, ESI MS/MS, MALDI MS, methylation-GC-MS, Pseudallescheria boydii mycelia, methylation GC-MS, Psedallescheria boydii

Structure type: oligomer ; 983.5 [M+Na]+
Location inside paper: p.899, O-I, table II, fig.3, fig. 4, fig. 5, fig. 6
Aglycon: protein
Compound class: O-glycoprotein
Contained glycoepitopes: IEDB_114705,IEDB_130701,IEDB_136105,IEDB_136906,IEDB_137472,IEDB_1394181,IEDB_1394182,IEDB_141794,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_145010,IEDB_146664,IEDB_151528,IEDB_152206,IEDB_190606,IEDB_225177,IEDB_885823,IEDB_983930,IEDB_983931,SB_192,SB_44,SB_67,SB_7,SB_72

Methods: 13C NMR, 1H NMR, methylation, NMR-2D, GC-MS, ELISA, ESI-MS, acid hydrolysis, ESI-MS/MS, MALDI-TOF MS, NMR-1D, extraction, HPTLC, methylation analysis, SEC, alkaline reductive hydrolysis, Hapten inhibition test, hapten inhibition test
Biological activity: isolated oligosaccharide alditols blocked recognition between rabbit sera and intact peptidorhamnomannan in a dose-dependent manner

Related record ID(s): 40523, 40756, 43364
NCBI Taxonomy refs (TaxIDs): 5597
Reference(s) to other database(s): GTC:G25012MR
Show glycosyltransferases

NMR conditions: in D2O at 303 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,3	a?Rhap	105.3	73.0	73.0	74.8	72.0	19.4
2,3	a?Rhap	99.3	73.0	81.2	74.1	71.8	19.4
2	a?Manp	104.0	69.3	77.7	70.2	76.1	63.0
6,4	a?Glcp	102.9	74.7	75.6	72.2	74.8	63.0
6	a?Galp	106.4	73.8	75.0	80.0	78.0	64.0
	x?Man-ol	63.0	82.5	70.2	?	?	74.5


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,3	a?Rhap	5.08	4.10	3.88	3.49	3.88	1.32
2,3	a?Rhap	4.99	4.12	3.93	3.58	4.03	1.30
2	a?Manp	5.08	4.21	3.94	3.77	3.89	3.80-3.85
6,4	a?Glcp	4.98	3.56	3.79	3.49	4.17	3.80-3.85
6	a?Galp	4.52	3.63	3.78	4.06	3.82	3.93-3.97
	x?Man-ol	3.80-3.90	3.83	4.07	?	?	3.82-4.23


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,3,3	a?Rhap	105.3/5.08	73.0/4.10	73.0/3.88	74.8/3.49	72.0/3.88	19.4/1.32
2,3	a?Rhap	99.3/4.99	73.0/4.12	81.2/3.93	74.1/3.58	71.8/4.03	19.4/1.30
2	a?Manp	104.0/5.08	69.3/4.21	77.7/3.94	70.2/3.77	76.1/3.89	63.0/3.80-3.85
6,4	a?Glcp	102.9/4.98	74.7/3.56	75.6/3.79	72.2/3.49	74.8/4.17	63.0/3.80-3.85
6	a?Galp	106.4/4.52	73.8/3.63	75.0/3.78	80.0/4.06	78.0/3.82	64.0/3.93-3.97
	x?Man-ol	63.0/3.80-3.90	82.5/3.83	70.2/4.07	?/?	?/?	74.5/3.82-4.23

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,3	a?Rhap	5.08	4.10	3.88	3.49	3.88	1.32
2,3	a?Rhap	4.99	4.12	3.93	3.58	4.03	1.30
2	a?Manp	5.08	4.21	3.94	3.77	3.89	3.80 3.85
6,4	a?Glcp	4.98	3.56	3.79	3.49	4.17	3.80 3.85
6	a?Galp	4.52	3.63	3.78	4.06	3.82	3.93 3.97
	x?Man-ol	3.80 3.90	3.83	4.07	?	?	3.82 4.23

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,3	a?Rhap	105.3	73.0	73.0	74.8	72.0	19.4
2,3	a?Rhap	99.3	73.0	81.2	74.1	71.8	19.4
2	a?Manp	104.0	69.3	77.7	70.2	76.1	63.0
6,4	a?Glcp	102.9	74.7	75.6	72.2	74.8	63.0
6	a?Galp	106.4	73.8	75.0	80.0	78.0	64.0
	x?Man-ol	63.0	82.5	70.2	?	?	74.5

The spectrum also has 2 signals at unknown positions (not plotted).

There are 64 chemically distinct structures. Please, select:

C[C@H]1O[C@H](O[C@@H]2[C@H](O)[C@@H](O[C@@H]3[C@H](O)[C@@H](O[C@H](CO)[C@@H](O)[C@H](O)[C@H](O)CO[C@H]4O[C@H](CO)[C@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)O[C@H](CO)[C@H]3O)O[C@H](C)[C@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize