Bioorthogonal human milk oligosaccharide probes for antimicrobial target identification within Streptococcus agalactiae

• Published in: Carbohydrate research Vol. 488; p. 107895
• Main Authors: Chambers, Schuyler A., Townsend, Steven D.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 01.02.2020; Elsevier
• Subjects: Antibacterial activity; Biochemistry & Molecular Biology; Bioorthogonal probes; Chemistry; Chemistry, Applied; Chemistry, Organic; Group B Streptococcus; Human milk oligosaccharides; Life Sciences & Biomedicine; Physical Sciences; Science & Technology; Antibacterial activity; Human milk oligosaccharides; Group B Streptococcus; Bioorthogonal probes; PHOTO-CROSS-LINKING; DIAZIRINE
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2019.107895

Human milk oligosaccharides (HMOs) are a structurally diverse class of carbohydrates that possess strong antibacterial activity against Streptococcus agalactiae (Group B Strep, GBS). This work highlights the design, synthesis, and retained biological activity of several HMO bioorthogonal probes within GBS, a first in class advance. The use of such probes will assist in identifying HMO-protein interactions within GBS and may be broadly applicable in researching HMO cellular targets within a variety of biological systems. Finally, this strategy is highly amenable to other oligosaccharide scaffolds, requiring minimal synthetic transformations and chemical perturbation. [Display omitted] •2-step conversion of deprotected oligosaccharides into bioorthogonal probes.•Broad spectrum applicability to oligosaccharide scaffolds.•Retained antibacterial properties.•Applications to human milk derived oligosaccharides.