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CHEBI:194239 - β-D-Glcp-(1→6)-[α-L-Rhap-(1→3)]-α-D-Glcp-(1→3)-α-L-Rhap2Ac-(1→3)-β-D-GlcpNAcO[CH2]2NH2

ChEBI IDCHEBI:194239
ChEBI Nameβ-D-Glcp-(1→6)-[α-L-Rhap-(1→3)]-α-D-Glcp-(1→3)-α-L-Rhap2Ac-(1→3)-β-D-GlcpNAcO[CH2]2NH2
Stars
ASCII Namebeta-D-Glcp-(1->6)-[alpha-L-Rhap-(1->3)]-alpha-D-Glcp-(1->3)-alpha-L-Rhap2Ac-(1->3)-beta-D-GlcpNAcO[CH2]2NH2
DefinitionA synthetic β-D-glucoside that is a branched pentasaccharide derivative consisting of two glucose residues, two rhamnose residues (out of which one is acetylated at the 2nd position) and one N-acetylglucosamine residue with at the reducing end an aminoethyl linker allowing for efficient conjugation to a carrier protein. The basic structure (i.e. without the linker) is the pentasaccharide repeat unit of the O25B major serotype within the extraintestinal pathogenic E. coli (ExPEC) group which expresses a unique O-antigen.
Last Modified25 January 2023
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC36H62N2O25
Net Charge0
Average Mass922.881
Monoisotopic Mass922.36417
SMILESCC(=O)N[C@H]1[C@H](OCCN)O[C@H](CO)[C@@H](O)[C@@H]1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O[C@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](O)[C@H]3O)[C@H]2O)[C@H]1OC(C)=O
InChIInChI=1S/C36H62N2O25/c1-10-18(43)23(48)26(51)34(55-10)62-29-22(47)16(9-54-33-25(50)24(49)20(45)14(7-39)59-33)60-35(27(29)52)63-30-19(44)11(2)56-36(31(30)57-13(4)42)61-28-17(38-12(3)41)32(53-6-5-37)58-15(8-40)21(28)46/h10-11,14-36,39-40,43-52H,5-9,37H2,1-4H3,(H,38,41)/t10-,11-,14+,15+,16+,17+,18-,19-,20+,21+,22+,23+,24-,25+,26+,27+,28+,29-,30+,31+,32+,33+,34-,35+,36-/m0/s1
InChIKeyCXSAQTXAWJBZBM-YTXWRZJASA-N
Roles Classification
Biological Role:
antigen  Any substance that stimulates an immune response in the body, such as through antibody production or by presentation to a T-cell receptor after binding to a major histocompability complex (MHC).
ChEBI Ontology
Outgoing Relation(s)
β-D-Glcp-(1→6)-[α-L-Rhap-(1→3)]-α-D-Glcp-(1→3)-α-L-Rhap2Ac-(1→3)-β-D-GlcpNAcO[CH2]2NH2 (CHEBI:194239) has role antigen (CHEBI:59132)
β-D-Glcp-(1→6)-[α-L-Rhap-(1→3)]-α-D-Glcp-(1→3)-α-L-Rhap2Ac-(1→3)-β-D-GlcpNAcO[CH2]2NH2 (CHEBI:194239) is a β-D-glucoside (CHEBI:22798)
IUPAC Name 
2-aminoethyl β-D-glucopyranosyl-(1→6)-[α-L-rhamnopyranosyl-(1→3)]-α-D-glucopyranosyl-(1→3)-2-O-acetyl-6-deoxy-α-L-mannopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranoside
Synonyms  Source
2-aminoethyl 6-deoxy-α-L-mannopyranosyl-(1→3)-[β-D-glucopyranosyl-(1→6)]-α-D-glucopyranosyl-(1→3)-2-O-acetyl-6-deoxy-α-L-mannopyranosyl-(1→3)-2-acetamido-2-deoxy-β-D-glucopyranosideIUPAC
β-D-Glc-(1→6)-[α-L-Rha-(1→3)]-α-D-Glc-(1→3)-α-L-Rha2Ac-(1→3)-β-D-GlcNAcO[CH2]2NH2ChEBI
2-aminoethyl β-D-glucosyl-(1→6)-[α-L-rhamnosyl-(1→3)]-α-D-glucosyl-(1→3)-2-O-acetyl-α-L-rhamnosyl-(1→3)-N-acetyl-β-D-glucosaminideChEBI
Glcβ1-6(Rhaα1-3)Glcα1-3Rha2Acα1-3GlcNAcβO[CH2]2NH2IUPAC
Citations