Regioselective Glycosylation Strategies for the Synthesis of Group Ia and Ib Streptococcus Related Glycans Enable Elucidating Unique Conformations of the Capsular Polysaccharides.
carbohydrates
conformation analysis
glycosylation
regioselectivity
therapeutics
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
18 Dec 2019
18 Dec 2019
Historique:
received:
02
08
2019
revised:
07
09
2019
pubmed:
12
9
2019
medline:
26
12
2019
entrez:
12
9
2019
Statut:
ppublish
Résumé
Group B Streptococcus serotypes Ia and Ib capsular polysaccharides are key targets for vaccine development. In spite of their immunospecifity these polysaccharides share high structural similarity. Both are composed of the same monosaccharide residues and differ only in the connection of the Neu5Acα2-3Gal side chain to the GlcNAc unit, which is a β1-4 linkage in serotype Ia and a β1-3 linkage in serotype Ib. The development of efficient regioselective routes for GlcNAcβ1-3[Glcβ1-4]Gal synthons is described, which give access to different group B Streptococcus (GBS) Ia and Ib repeating unit frameshifts. These glycans were used to probe the conformation and molecular dynamics of the two polysaccharides, highlighting the different presentation of the protruding Neu5Acα2-3Gal moieties on the polysaccharide backbones and a higher flexibility of Ib polymer relative to Ia, which can impact epitope exposure.
Identifiants
pubmed: 31506992
doi: 10.1002/chem.201903527
pmc: PMC6972993
doi:
Substances chimiques
Polysaccharides, Bacterial
0
Glucosamine
N08U5BOQ1K
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
16277-16287Subventions
Organisme : European Metrology Programme for Innovation and Research
ID : 675671
Organisme : Horizon 2020 Framework Programme
ID : 675671
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
Angew Chem Int Ed Engl. 2014 Sep 1;53(36):9597-602
pubmed: 25044775
J Pharm Biomed Anal. 2014 Sep;98:9-15
pubmed: 24873733
Angew Chem Int Ed Engl. 2019 May 27;58(22):7268-7272
pubmed: 30942512
Carbohydr Res. 2008 Jul 21;343(10-11):1540-52
pubmed: 18452900
Clin Exp Vaccine Res. 2018 Jan;7(1):76-81
pubmed: 29399583
Chem Rev. 2018 Dec 12;118(23):11457-11517
pubmed: 30507165
J Infect Dis. 2014 Mar 1;209(5):781-8
pubmed: 24133184
J Org Chem. 2001 Apr 20;66(8):2547-54
pubmed: 11304169
Carbohydr Res. 2005 Apr 11;340(5):1007-18
pubmed: 15780265
Carbohydr Res. 2017 Feb 22;440-441:43-50
pubmed: 28214389
Clin Transl Immunology. 2016 Aug 26;5(8):e99
pubmed: 27588204
Biochemistry. 1983 Mar 1;22(5):1258-64
pubmed: 6838851
Org Lett. 2015 Mar 6;17(5):1102-5
pubmed: 25674920
Carbohydr Res. 2010 Apr 19;345(6):750-60
pubmed: 20170905
Carbohydr Res. 2003 Mar 14;338(6):503-14
pubmed: 12668106
Proc Natl Acad Sci U S A. 2017 May 9;114(19):5017-5022
pubmed: 28439022
Vaccine. 2013 Aug 28;31 Suppl 4:D7-12
pubmed: 23973349
Lancet Infect Dis. 2016 Aug;16(8):923-34
pubmed: 27139805
Chem Soc Rev. 2019 Aug 27;48(17):4688-4706
pubmed: 31287452
European J Org Chem. 2018 Sep 9;2018(33):4548-4555
pubmed: 30443159
Expert Opin Biol Ther. 2003 Sep;3(6):975-84
pubmed: 12943456
Ther Adv Vaccines. 2015 May;3(3):76-90
pubmed: 26288735
Chemistry. 2019 Dec 18;25(71):16277-16287
pubmed: 31506992
J Immunol. 1985 Dec;135(6):4164-70
pubmed: 3934276
J Bacteriol. 2005 Jul;187(13):4615-26
pubmed: 15968073
Microbiol Spectr. 2019 Mar;7(2):
pubmed: 30873933
Org Biomol Chem. 2019 May 28;17(20):4934-4950
pubmed: 31044205
Acc Chem Res. 2017 May 16;50(5):1270-1279
pubmed: 28463499
Chemistry. 2010 Feb 8;16(6):1754-60
pubmed: 20066711
Pharmaceuticals (Basel). 2019 Feb 13;12(1):
pubmed: 30781826
Biochemistry. 1981 Aug 4;20(16):4511-8
pubmed: 6170311
Angew Chem Int Ed Engl. 2018 Jul 2;57(27):8240-8244
pubmed: 29603532
Chem Biol. 2014 Jan 16;21(1):38-50
pubmed: 24439205