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Taxonomic group: bacteria / Firmicutes (Phylum: Firmicutes)
Associated disease: infection due to Bacillus anthracis [ICD11: XN94F

]

The structure was elucidated in this paper
NCBI PubMed ID: 16275067
Publication DOI: 10.1016/j.bmcl.2005.10.056
Journal NLM ID: 9107377
Publisher: Elsevier
Correspondence: kpn

helix.nih.gov
Institutions: National Institute of Diabetes and Digestive and Kidney Disease/LMC, National Institutes of Health, Bethesda, MD 20892-0815, USA

An alpha-glycoside of the tetrasaccharide sequence β-Ant-(1→3)-α-L-Rhap-(1→3)-α-L-Rhap-(1→2)-α-L-Rhap whose aglycon allows conjugation to suitable carriers was synthesized. The NMR characteristics of the compound are virtually identical with those of the α-anomer of the tetrasaccharide isolated from the major glycoprotein of the Bacillus anthracis exosporium. Thus, the correct structure of the natural product has been proven by chemical synthesis.

oligosaccharide, Anthrax, Anthrose, Exosporium glycoprotein, Thioglycoside

Structure type: oligomer
Location inside paper: abstract, p.616, Scheme 1, compound 20
Aglycon: ->6) methyl 6-hydroxyhexanoate
Trivial name: tetrasaccharide side chain of glycoprotein
Contained glycoepitopes: IEDB_133754,IEDB_136105,IEDB_146675,IEDB_146676,IEDB_150074,IEDB_225177,IEDB_885823

Methods: NMR, chemical methods
Synthetic data: chemical
Comments, role: Sug's trivial name is anthrose (Ant)

NCBI Taxonomy refs (TaxIDs): 1392
Reference(s) to other database(s): GlycomeDB:37212
Show glycosyltransferases

NMR conditions: in DMSO-d6 at 298 K [as TSV]

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,3,4	lX3HOiVl	171.45	48.67	68.71	29.48-29.58	60.16
2,3,3,2	Me	60.16
2,3,3	bDQuip4N	103.4	84.36	72.77	56.42	70.34	18.18
2,3	aLRhap	101.71	69.67	79.48	71.65	68.31	17.73
2	aLRhap	101.76	69.97	76.28	71.37	69.04	17.81
	aLRhap	98.62	76.66	70.56	72.22	68.58	18.02


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,3,4	lX3HOiVl	-	2.204	-	1.155	1.143
2,3,3,2	Me	3.519
2,3,3	bDQuip4N	4.577	2.845	3.281	3.402	3.275	1.074
2,3	aLRhap	4.857	3.872	3.745	3.402	3.636	1.132
2	aLRhap	4.842	3.775	3.609	3.325	3.487	1.101
	aLRhap	4.566	3.634	3.530	3.155	3.373	1.134


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
2,3,3,4	lX3HOiVl		48.67/2.204		29.48-29.58/1.155	60.16/1.143
2,3,3,2	Me	60.16/3.519
2,3,3	bDQuip4N	103.4/4.577	84.36/2.845	72.77/3.281	56.42/3.402	70.34/3.275	18.18/1.074
2,3	aLRhap	101.71/4.857	69.67/3.872	79.48/3.745	71.65/3.402	68.31/3.636	17.73/1.132
2	aLRhap	101.76/4.842	69.97/3.775	76.28/3.609	71.37/3.325	69.04/3.487	17.81/1.101
	aLRhap	98.62/4.566	76.66/3.634	70.56/3.530	72.22/3.155	68.58/3.373	18.02/1.134

¹H NMR data:

Linkage	Residue	H1	H2	H3	H4	H5	H6
2,3,3,4	lX3HOiVl		2.204		1.155	1.143
2,3,3,2	Me	3.519
2,3,3	bDQuip4N	4.577	2.845	3.281	3.402	3.275	1.074
2,3	aLRhap	4.857	3.872	3.745	3.402	3.636	1.132
2	aLRhap	4.842	3.775	3.609	3.325	3.487	1.101
	aLRhap	4.566	3.634	3.530	3.155	3.373	1.134

¹³C NMR data:

Linkage	Residue	C1	C2	C3	C4	C5	C6
2,3,3,4	lX3HOiVl	171.45	48.67	68.71	29.48 29.58	60.16
2,3,3,2	Me	60.16
2,3,3	bDQuip4N	103.4	84.36	72.77	56.42	70.34	18.18
2,3	aLRhap	101.71	69.67	79.48	71.65	68.31	17.73
2	aLRhap	101.76	69.97	76.28	71.37	69.04	17.81
	aLRhap	98.62	76.66	70.56	72.22	68.58	18.02

There is only one chemically distinct structure:

CO[C@H]1[C@H](O[C@@H]2[C@@H](O)[C@H](C)O[C@@H](O[C@@H]3[C@@H](O)[C@H](C)O[C@@H](O[C@H]4[C@H](O)O[C@@H](C)[C@H](O)[C@H]4O)[C@@H]3O)[C@@H]2O)O[C@H](C)[C@@H](NC(=O)CC(C)(C)O)[C@@H]1O

SVG MW SMILES 3D mol Ionize