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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Organ / tissue: cell wall

The structure was elucidated in this paper
Publication DOI: 10.1016/S0008-6215(01)00273-7
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: mbernabe

iqog.csic.es
Institutions: Centro de Investigaciones Biológicas, CSIC, Velázquez 144, 28006-Madrid, Spain

The structure of a cell wall alkali-extractable and water-soluble polysaccharide isolated from two species of Arachniotus has been established by reductive cleavage and NMR spectroscopy. The linear polysaccharide consists of a regular disaccharide-repeating unit with the structure: [-->6)-beta-D-Galf-(1-->5)-beta-D-Galf-(1-->](n)-->mannan core.

polysaccharides, NMR spectroscopy, chemotaxonomy, Arachniotus

Structure type: polymer chemical repeating unit
Location inside paper: p. 327, F1SS
Aglycon: mannan core
Contained glycoepitopes: IEDB_136095,IEDB_137472,IEDB_149176,IEDB_190606,IEDB_885812

Methods: 13C NMR, 1H NMR, GC-MS, acid hydrolysis, GLC, TOCSY, methylation analysis, HMBC, HMQC, NOESY, DGF-COSY

NCBI Taxonomy refs (TaxIDs): 166107, 880165
Reference(s) to other database(s): GTC:G61425HH
Show glycosyltransferases

NMR conditions: in D2O at 313 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
5	bDGalf	107.9	82.2	77.7	84.2	70.6	70.3
	bDGalf	108.9	82.0	77.7	83.0	76.7	62.0


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
5	bDGalf	5.24	4.16	4.09	4.08	3.98	3.65-3.88
	bDGalf	5.04	4.14	4.13	4.12	3.97	3.81-3.82


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
5	bDGalf	107.9/5.24	82.2/4.16	77.7/4.09	84.2/4.08	70.6/3.98	70.3/3.65-3.88
	bDGalf	108.9/5.04	82.0/4.14	77.7/4.13	83.0/4.12	76.7/3.97	62.0/3.81-3.82

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
5	bDGalf	5.24	4.16	4.09	4.08	3.98	3.65 3.88
	bDGalf	5.04	4.14	4.13	4.12	3.97	3.81 3.82

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
5	bDGalf	107.9	82.2	77.7	84.2	70.6	70.3
	bDGalf	108.9	82.0	77.7	83.0	76.7	62.0

There is only one chemically distinct structure:

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

SVG MW SMILES 3D mol Ionize

Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Organ / tissue: cell wall

The structure was elucidated in this paper
Journal NLM ID: 0043535
WWW link: http://www.sciencedirect.com/science/article/pii/S0008621502002938
Publisher: Elsevier
Correspondence: mbernabe

iqog.csic.es
Institutions: Centro de Investigaciones Biologicas, CSIC, Velazquez 144, 28006 Madrid, Spain, Departamento de Quımica Orgánica Biológica, Instituto de Quımica Orgánica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain

The alkali-extracted water-soluble galactomannan FISS isolated from the cell wall of two species each of Geotrichum, Galactomyces, and Dipodascus have been studied by methylation analysis and NMR spectroscopy, and their structure is established as the following: [structure].

polysaccharides, NMR spectroscopy, fungi, Geotrichum, Dipodascus, Galactomyces

Structure type: polymer chemical repeating unit ; n=12
Location inside paper: abstract, F1SS
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_140116,IEDB_141793,IEDB_141794,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_151528,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_190606,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_7,SB_72

Methods: 13C NMR, 1H NMR, GC-MS, acid hydrolysis, GLC, MALDI-TOF, TOCSY, methylation analysis, partial acetolysis, HMBC, HMQC, NOESY, HSQC-TOCSY, DGF-COSY

NCBI Taxonomy refs (TaxIDs): 58640, 44066, 1173061, 43985, 43962, 43976
Reference(s) to other database(s): GTC:G64007KY
Show glycosyltransferases

NMR conditions: in D2O at 313 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,6,6,6,6,6,6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,6,6,6,6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6,6,6,6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,6,6,6,6,6,6,2,2	aDGalp
6,6,6,6,6,6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6,6,6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,6,6,6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,6,6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6,6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,6,6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
	aDManp	100.4	?	?	?	?	?


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,6,6,6,6,6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,6,6,6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78-3.88
6,6,6,6,6,6,6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68-4.03
6,6,6,6,6,6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,6,6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78-3.88
6,6,6,6,6,6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68-4.03
6,6,6,6,6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78-3.88
6,6,6,6,6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68-4.03
6,6,6,6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78-3.88
6,6,6,6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68-4.03
6,6,6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78-3.88
6,6,6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68-4.03
6,6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78-3.88
6,6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68-4.03
6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78-3.88
6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68-4.03
6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78-3.88
6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68-4.03
6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78-3.88
6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68-4.03
6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78-3.88
6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68-4.03
	aDManp	4.92	4.01	?	?	?	?


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6,6,6,6,6,6,6,6,6,6,2,2	aDGalp	102.1/5.17	69.8/3.83	70.3/3.91	70.3/4.01	72.3/4.09	62.3/3.75
6,6,6,6,6,6,6,6,6,6,2	aDManp	101.5/5.37	80.3/4.11	71.6/3.92	68.0/3.77	74.2/3.77	62.0/3.78-3.88
6,6,6,6,6,6,6,6,6,6	aDManp	99.2/5.09	79.7/4.03	71.6/3.93	67.4/3.82	72.2/3.83	66.7/3.68-4.03
6,6,6,6,6,6,6,6,6,2,2	aDGalp	NMR TSV error 2: unequal length of 13C and 1H datasets
6,6,6,6,6,6,6,6,6,2	aDManp	101.5/5.37	80.3/4.11	71.6/3.92	68.0/3.77	74.2/3.77	62.0/3.78-3.88
6,6,6,6,6,6,6,6,6	aDManp	99.2/5.09	79.7/4.03	71.6/3.93	67.4/3.82	72.2/3.83	66.7/3.68-4.03
6,6,6,6,6,6,6,6,2,2	aDGalp	102.1/5.17	69.8/3.83	70.3/3.91	70.3/4.01	72.3/4.09	62.3/3.75
6,6,6,6,6,6,6,6,2	aDManp	101.5/5.37	80.3/4.11	71.6/3.92	68.0/3.77	74.2/3.77	62.0/3.78-3.88
6,6,6,6,6,6,6,6	aDManp	99.2/5.09	79.7/4.03	71.6/3.93	67.4/3.82	72.2/3.83	66.7/3.68-4.03
6,6,6,6,6,6,6,2,2	aDGalp	102.1/5.17	69.8/3.83	70.3/3.91	70.3/4.01	72.3/4.09	62.3/3.75
6,6,6,6,6,6,6,2	aDManp	101.5/5.37	80.3/4.11	71.6/3.92	68.0/3.77	74.2/3.77	62.0/3.78-3.88
6,6,6,6,6,6,6	aDManp	99.2/5.09	79.7/4.03	71.6/3.93	67.4/3.82	72.2/3.83	66.7/3.68-4.03
6,6,6,6,6,6,2,2	aDGalp	102.1/5.17	69.8/3.83	70.3/3.91	70.3/4.01	72.3/4.09	62.3/3.75
6,6,6,6,6,6,2	aDManp	101.5/5.37	80.3/4.11	71.6/3.92	68.0/3.77	74.2/3.77	62.0/3.78-3.88
6,6,6,6,6,6	aDManp	99.2/5.09	79.7/4.03	71.6/3.93	67.4/3.82	72.2/3.83	66.7/3.68-4.03
6,6,6,6,6,2,2	aDGalp	102.1/5.17	69.8/3.83	70.3/3.91	70.3/4.01	72.3/4.09	62.3/3.75
6,6,6,6,6,2	aDManp	101.5/5.37	80.3/4.11	71.6/3.92	68.0/3.77	74.2/3.77	62.0/3.78-3.88
6,6,6,6,6	aDManp	99.2/5.09	79.7/4.03	71.6/3.93	67.4/3.82	72.2/3.83	66.7/3.68-4.03
6,6,6,6,2,2	aDGalp	102.1/5.17	69.8/3.83	70.3/3.91	70.3/4.01	72.3/4.09	62.3/3.75
6,6,6,6,2	aDManp	101.5/5.37	80.3/4.11	71.6/3.92	68.0/3.77	74.2/3.77	62.0/3.78-3.88
6,6,6,6	aDManp	99.2/5.09	79.7/4.03	71.6/3.93	67.4/3.82	72.2/3.83	66.7/3.68-4.03
6,6,6,2,2	aDGalp	102.1/5.17	69.8/3.83	70.3/3.91	70.3/4.01	72.3/4.09	62.3/3.75
6,6,6,2	aDManp	101.5/5.37	80.3/4.11	71.6/3.92	68.0/3.77	74.2/3.77	62.0/3.78-3.88
6,6,6	aDManp	99.2/5.09	79.7/4.03	71.6/3.93	67.4/3.82	72.2/3.83	66.7/3.68-4.03
6,6,2,2	aDGalp	102.1/5.17	69.8/3.83	70.3/3.91	70.3/4.01	72.3/4.09	62.3/3.75
6,6,2	aDManp	101.5/5.37	80.3/4.11	71.6/3.92	68.0/3.77	74.2/3.77	62.0/3.78-3.88
6,6	aDManp	99.2/5.09	79.7/4.03	71.6/3.93	67.4/3.82	72.2/3.83	66.7/3.68-4.03
6,2,2	aDGalp	102.1/5.17	69.8/3.83	70.3/3.91	70.3/4.01	72.3/4.09	62.3/3.75
6,2	aDManp	101.5/5.37	80.3/4.11	71.6/3.92	68.0/3.77	74.2/3.77	62.0/3.78-3.88
6	aDManp	99.2/5.09	79.7/4.03	71.6/3.93	67.4/3.82	72.2/3.83	66.7/3.68-4.03
	aDManp	100.4/4.92	?/4.01	?/?	?/?	?/?	?/?

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,6,6,6,6,6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,6,6,6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78 3.88
6,6,6,6,6,6,6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68 4.03
6,6,6,6,6,6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,6,6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78 3.88
6,6,6,6,6,6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68 4.03
6,6,6,6,6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78 3.88
6,6,6,6,6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68 4.03
6,6,6,6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78 3.88
6,6,6,6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68 4.03
6,6,6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78 3.88
6,6,6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68 4.03
6,6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78 3.88
6,6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68 4.03
6,6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78 3.88
6,6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68 4.03
6,6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78 3.88
6,6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68 4.03
6,6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78 3.88
6,6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68 4.03
6,2,2	aDGalp	5.17	3.83	3.91	4.01	4.09	3.75
6,2	aDManp	5.37	4.11	3.92	3.77	3.77	3.78 3.88
6	aDManp	5.09	4.03	3.93	3.82	3.83	3.68 4.03
	aDManp	4.92	4.01	?	?	?	?

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,6,6,6,6,6,6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,6,6,6,6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6,6,6,6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,6,6,6,6,6,6,2,2	aDGalp
6,6,6,6,6,6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6,6,6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,6,6,6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,6,6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6,6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,6,6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6,6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
6,2,2	aDGalp	102.1	69.8	70.3	70.3	72.3	62.3
6,2	aDManp	101.5	80.3	71.6	68.0	74.2	62.0
6	aDManp	99.2	79.7	71.6	67.4	72.2	66.7
	aDManp	100.4	?	?	?	?	?

The spectrum also has 5 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

[*]OC[C@H]1O[C@H](OC[C@H]2O[C@H](OC[C@H]3O[C@H](OC[C@H]4O[C@H](OC[C@H]5O[C@H](OC[C@H]6O[C@H](OC[C@H]7O[C@H](OC[C@H]8O[C@H](OC[C@H]9O[C@H](OC[C@H]%10O[C@H](OC[C@H]%11O[C@H]([*])[C@@H](O)[C@@H](O)[C@@H]%11O)[C@@H](O[C@H]%11O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%11O[C@H]%11O[C@H](CO)[C@H](O)[C@H](O)[C@H]%11O)[C@@H](O)[C@@H]%10O)[C@@H](O[C@H]%10O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%10O[C@H]%10O[C@H](CO)[C@H](O)[C@H](O)[C@H]%10O)[C@@H](O)[C@@H]9O)[C@@H](O[C@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]9O[C@H]9O[C@H](CO)[C@H](O)[C@H](O)[C@H]9O)[C@@H](O)[C@@H]8O)[C@@H](O[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]8O[C@H]8O[C@H](CO)[C@H](O)[C@H](O)[C@H]8O)[C@@H](O)[C@@H]7O)[C@@H](O[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]7O[C@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)[C@@H](O)[C@@H]6O)[C@@H](O[C@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]6O[C@H]6O[C@H](CO)[C@H](O)[C@H](O)[C@H]6O)[C@@H](O)[C@@H]5O)[C@@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]5O[C@H]5O[C@H](CO)[C@H](O)[C@H](O)[C@H]5O)[C@@H](O)[C@@H]4O)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@@H]3O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@@H]2O)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize

Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Organ / tissue: cell wall

The structure was elucidated in this paper
Publication DOI: 10.1016/S0008-6215(01)00140-9
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: mbernabe

iqog.csic.es
Institutions: Departamento de Quı́mica Orgánica Biológica, Instituto de Quı́mica Orgánica, CSIC, Juan de la Cierva 3, E-28006 Madrid, Spain, Centro de Investigaciones Biológica, CSIC, Velázquez 144, E-28006, Madrid, Spain

The structure of a polysaccharide isolated from the cell wall of Hypocrea gelatinosa has been investigated by means of chemical analyses and 1D and 2D NMR spectroscopy. The polysacharide has an irregular structure, idealized as follows: [structure].

polysaccharides, NMR spectroscopy, fungi, Hypocrea gelatinosa

Structure type: structural motif or average structure
Location inside paper: p. 177
Trivial name: cell wall heteromannan
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_115136,IEDB_130701,IEDB_136095,IEDB_137472,IEDB_140116,IEDB_140630,IEDB_141793,IEDB_141828,IEDB_142488,IEDB_144983,IEDB_144998,IEDB_146664,IEDB_149176,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_190606,IEDB_76933,IEDB_983930,IEDB_983931,SB_192,SB_198,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, partial acid hydrolysis, acid hydrolysis, GLC, TOCSY, methylation analysis, reduction, HMBC, HMQC, HSQC-TOCSY, DGF-COSY
Comments, role: number of non-branched Man residues in the backbone chain may vary

NCBI Taxonomy refs (TaxIDs): 1490988
Reference(s) to other database(s): GTC:G62060OZ
Show glycosyltransferases

NMR conditions: in D2O at 313 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,2,6,2,4	aDGlcp	99.3	72.7-72.8	73.7	70.2	72.7-72.8	61.2
6,6,2,6,2	aDGlcpA	99.1	71.7-71.8	74.3	77.6-77.8	73.8	176.5
6,6,2,6	bDGalf	107.3	87.7	76.5	83.4	71.5-71.8	63.8
6,6,2	bDGalf	106.8-106.9	82.0	77.6-77.8	84.0-84.3	70.9	70.0
6,6	aDManp	98.0	75.7	70.7	67.7	71.9	66.4
6	aDManp	100.4	71.0	?	?	?	?
2	bDGalf	106.8-106.9	82.0	77.6-77.8	84.0-84.3	71.5-71.8	63.6
	aDManp	98.0	75.7	70.7	67.7	71.9	66.4


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,2,6,2,4	aDGlcp	5.46	3.53	3.71	3.40	3.73	3.78-3.82
6,6,2,6,2	aDGlcpA	5.07	3.63	3.92	3.78	4.12	-
6,6,2,6	bDGalf	5.17	4.17	4.26	4.02	3.88	3.65-3.72
6,6,2	bDGalf	5.12	4.16	4.09	4.08	3.97	3.65-3.89
6,6	aDManp	5.04	4.07	3.87	3.80	3.81	?
6	aDManp	4.90	3.97	?	?	?	?
2	bDGalf	5.12	4.16	4.10	4.10	3.85	3.67-3.74
	aDManp	5.04	4.07	3.87	3.80	3.81	?


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
6,6,2,6,2,4	aDGlcp	99.3/5.46	72.7-72.8/3.53	73.7/3.71	70.2/3.40	72.7-72.8/3.73	61.2/3.78-3.82
6,6,2,6,2	aDGlcpA	99.1/5.07	71.7-71.8/3.63	74.3/3.92	77.6-77.8/3.78	73.8/4.12	
6,6,2,6	bDGalf	107.3/5.17	87.7/4.17	76.5/4.26	83.4/4.02	71.5-71.8/3.88	63.8/3.65-3.72
6,6,2	bDGalf	106.8-106.9/5.12	82.0/4.16	77.6-77.8/4.09	84.0-84.3/4.08	70.9/3.97	70.0/3.65-3.89
6,6	aDManp	98.0/5.04	75.7/4.07	70.7/3.87	67.7/3.80	71.9/3.81	66.4/?
6	aDManp	100.4/4.90	71.0/3.97	?/?	?/?	?/?	?/?
2	bDGalf	106.8-106.9/5.12	82.0/4.16	77.6-77.8/4.10	84.0-84.3/4.10	71.5-71.8/3.85	63.6/3.67-3.74
	aDManp	98.0/5.04	75.7/4.07	70.7/3.87	67.7/3.80	71.9/3.81	66.4/?

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
6,6,2,6,2,4	aDGlcp	5.46	3.53	3.71	3.40	3.73	3.78 3.82
6,6,2,6,2	aDGlcpA	5.07	3.63	3.92	3.78	4.12
6,6,2,6	bDGalf	5.17	4.17	4.26	4.02	3.88	3.65 3.72
6,6,2	bDGalf	5.12	4.16	4.09	4.08	3.97	3.65 3.89
6,6	aDManp	5.04	4.07	3.87	3.80	3.81	?
6	aDManp	4.90	3.97	?	?	?	?
2	bDGalf	5.12	4.16	4.10	4.10	3.85	3.67 3.74
	aDManp	5.04	4.07	3.87	3.80	3.81	?

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
6,6,2,6,2,4	aDGlcp	99.3	72.7 72.8	73.7	70.2	72.7 72.8	61.2
6,6,2,6,2	aDGlcpA	99.1	71.7 71.8	74.3	77.6 77.8	73.8	176.5
6,6,2,6	bDGalf	107.3	87.7	76.5	83.4	71.5 71.8	63.8
6,6,2	bDGalf	106.8 106.9	82.0	77.6 77.8	84.0 84.3	70.9	70.0
6,6	aDManp	98.0	75.7	70.7	67.7	71.9	66.4
6	aDManp	100.4	71.0	?	?	?	?
2	bDGalf	106.8 106.9	82.0	77.6 77.8	84.0 84.3	71.5 71.8	63.6
	aDManp	98.0	75.7	70.7	67.7	71.9	66.4

The spectrum also has 4 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

[*]OC[C@H]1O[C@H](OC[C@H]2O[C@H](OC[C@H]3O[C@H]([*])[C@@H](O[C@@H]4O[C@@H]([C@H](O)CO)[C@H](O)[C@H]4O)[C@@H](O)[C@@H]3O)[C@@H](O)[C@@H](O)[C@@H]2O)[C@@H](O[C@@H]2O[C@@H]([C@H](O)CO[C@@H]3O[C@@H]([C@H](O)CO)[C@H](O)[C@H]3O[C@H]3O[C@H](C(=O)O)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize