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CHEBI:157632 - S. pneumoniae serotype 14 capsular oligosaccharide derivative

ChEBI IDCHEBI:157632
ChEBI NameS. pneumoniae serotype 14 capsular oligosaccharide derivative
Stars
ASCII NameS. pneumoniae serotype 14 capsular oligosaccharide derivative
DefinitionA synthetic oligosaccharide derivative in which three β-D-Gal-(1→4)-β-D-Glc-(1→6)-[β-D-Gal-(1→4)]-β-D-GlcNAc tetrasaccharide units are linked through N-pentylpentanamide linkers, with a 5-aminopentyl spacer group attached to the GlcNAc residue within the terminal unit. Synthesised as a spacer-bridged oligosaccharide mimic of the capsular polysaccharide of Streptococcus pneumoniae serotype 14, the 5-aminopentyl spacer group affords a method of linking to the CRM197 carrier protein, a genetically detoxified form of diphtheria toxin.
Last Modified13 October 2020
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC108H188N6O67
Net Charge0
Average Mass2642.667
Monoisotopic Mass2641.14883
SMILESCC(=O)N[C@H]1[C@H](OCCCCCNC(=O)CCCCO[C@H]2[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]3[C@H](O)[C@@H](O)[C@H](OC[C@H]4O[C@@H](OCCCCCNC(=O)CCCCO[C@H]5[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]6[C@H](O)[C@@H](O)[C@H](OC[C@H]7O[C@@H](OCCCCCN)[C@H](NC(C)=O)[C@@H](O)[C@@H]7O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O)O[C@@H]6CO)[C@@H]5O)[C@H](NC(C)=O)[C@@H](O)[C@@H]4O[C@@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)O[C@@H]3CO)[C@@H]2O)O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO)[C@H](O)[C@H](OCCCCC(=O)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]1O
InChIInChI=1S/C108H188N6O67/c1-43(124)112-61-70(137)91(179-103-79(146)73(140)64(131)46(31-115)164-103)55(173-97(61)158-28-13-4-10-22-109)40-161-100-82(149)76(143)88(52(37-121)170-100)176-106-85(152)94(67(134)49(34-118)167-106)155-25-16-7-19-58(127)110-23-11-5-14-29-159-98-62(113-44(2)125)71(138)92(180-104-80(147)74(141)65(132)47(32-116)165-104)56(174-98)41-162-101-83(150)77(144)89(53(38-122)171-101)177-107-86(153)95(68(135)50(35-119)168-107)156-26-17-8-20-59(128)111-24-12-6-15-30-160-99-63(114-45(3)126)72(139)93(181-105-81(148)75(142)66(133)48(33-117)166-105)57(175-99)42-163-102-84(151)78(145)90(54(39-123)172-102)178-108-87(154)96(69(136)51(36-120)169-108)157-27-18-9-21-60(129)130/h46-57,61-108,115-123,131-154H,4-42,109H2,1-3H3,(H,110,127)(H,111,128)(H,112,124)(H,113,125)(H,114,126)(H,129,130)/t46-,47-,48-,49-,50-,51-,52-,53-,54-,55-,56-,57-,61-,62-,63-,64+,65+,66+,67+,68+,69+,70-,71-,72-,73+,74+,75+,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91-,92-,93-,94+,95+,96+,97-,98-,99-,100-,101-,102-,103+,104+,105+,106+,107+,108+/m1/s1
InChIKeyIITRGDMSEKBPGN-PEOYUYHUSA-N
Roles Classification
Biological Role:
mimotope  Any macromolecule whose structure mimics that of an epitope. When applied to immunisation, a mimotope induces the desired antibody specificities exclusively based on the principle of molecular mimicry.
ChEBI Ontology
Outgoing Relation(s)
S. pneumoniae serotype 14 capsular oligosaccharide derivative (CHEBI:157632) has role mimotope (CHEBI:60218)
S. pneumoniae serotype 14 capsular oligosaccharide derivative (CHEBI:157632) is a oligosaccharide derivative (CHEBI:63563)
IUPAC Name 
5-aminopentyl 3-O-{5-[(5-{[3-O-{5-[(5-{[3-O-(4-carboxybutyl)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-[β-D-galactopyranosyl-(1→4)]-2-acetamido-2-deoxy-β-D-glucopyranosyl]oxy}pentyl)amino]-5-oxopentyl}-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-[β-D-galactopyranosyl-(1→4)]-2-acetamido-2-deoxy-β-D-glucopyranosyl]oxy}pentyl)amino]-5-oxopentyl}-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→6)-[β-D-galactopyranosyl-(1→4)]-2-acetamido-2-deoxy-β-D-glucopyranoside
Synonyms  Source
3-O-{5-[(5-{[3-O-{5-[(5-{[3-O-(4-carboxybutyl)-β-D-Galp-(1→4)-β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]-β-D-GlcpNAc]oxy}pentyl)amino]-5-oxopentyl}-β-D-Galp-(1→4)-β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]-β-D-GlcpNAc]oxy}pentyl)amino]-5-oxopentyl}-β-D-Galp-(1→4)-β-D-Glcp-(1→6)-[β-D-Galp-(1→4)]-β-D-GlcpNAcO[CH2]5NH2ChEBI
3-O-{5-[(5-{[3-O-{5-[(5-{[3-O-(4-carboxybutyl)-β-D-Gal-(1→4)-β-D-Glc-(1→6)-[β-D-Gal-(1→4)]-β-D-GlcNAc]oxy}pentyl)amino]-5-oxopentyl}-β-D-Gal-(1→4)-β-D-Glc-(1→6)-[β-D-Gal-(1→4)]-β-D-GlcNAc]oxy}pentyl)amino]-5-oxopentyl}-β-D-Gal-(1→4)-β-D-Glc-(1→6)-[β-D-Gal-(1→4)]-β-D-GlcNAcO[CH2]5NH2ChEBI
Citations