Chemo-enzymatic synthesis of tetra-, penta-, and hexasaccharide fragments of the capsular polysaccharide of Streptococcus pneumoniae type 14.
The chemo-enzymatic synthesis is described of beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)]-beta-D-GlcpNAc-(1-->3)-beta-D-Galp-(1-->O(CH(2))(6)NH(2) (1), beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)]-beta-D-GlcpNAc-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->O(CH(2))(6)NH(2) (2), beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->O(CH(2))(6)NH(2) (3), and beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->3)-beta-D-Galp-(1-->4)-beta-D-Glcp-(1-->6)-[beta-D-Galp-(1-->4)]-beta-D-GlcpNAc-(1-->O(CH(2))(6)NH(2) (4), representing fragments of the repeating unit of the Streptococcus pneumoniae serotype 14 capsular polysaccharide. Linear intermediate oligosaccharides 5-8 were synthesized via chemical synthesis, followed by enzymatic galactosylation using bovine milk beta-1,4-galactosyltransferase as a catalyst. The title oligosaccharides form suitable compounds for conjugation with carrier proteins, to be tested as potential vaccines in animal models.
Joosten
John A F
JA
Bijvoet Center, Department of Bio-Organic Chemistry, Section of Glycoscience and Biocatalysis, Utrecht University, Padualaan 8, NL-3584 CH Utrecht, The Netherlands.
Lazet
Bart J
BJ
Kamerling
Johannis P
JP
Vliegenthart
Johannes F G
JF
D000818:Animals; D002240:Carbohydrate Sequence; D002417:Cattle; D005690:Galactose / Q000737:chemistry; D005944:Glucosamine / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009237:N-Acetyllactosamine Synthase / Q000378:metabolism; D009844:Oligosaccharides / Q000737:chemistry; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011135:Polysaccharides, Bacterial / Q000737:chemistry*; D013296:Streptococcus pneumoniae / Q000378:metabolism*
D009844:Oligosaccharides; D011134:Polysaccharides; D011135:Polysaccharides, Bacterial; D009237:N-Acetyllactosamine Synthase; D005944:Glucosamine; D005690:Galactose