Towards a New and Convenient Synthesis of Group B Streptococcus Type Ii (Gbs Ii) Repeating Unit

<none>

Programme Social programme Plenary speakers Keynote speakers 1st EuroCarb Young Researcher (ECYR) Workshop CarboMet Workshop Mini symposium: Glycobiology at the LUMC and beyond Favourites/Agenda

Social programme

Plenary speakers

Keynote speakers

1st EuroCarb Young Researcher (ECYR) Workshop

CarboMet Workshop

Mini symposium: Glycobiology at the LUMC and beyond

Favourites/Agenda

Photos

Venue & Travel Venue Accommodation City of Leiden Travel directions

Venue

Accommodation

City of Leiden

Travel directions

Committees

Home

Towards a New and Convenient Synthesis of Group B Streptococcus Type Ii (Gbs Ii) Repeating Unit

Meenakshi Singh 1 , Cinzia Colombo 1 , Luigi Lay 1

1 University Of Milan, Milan, Italy, 2 University Of Milan, Milan, italy, 3 University Of Milan, Milan, italy

Group B streptococcus (GBS) is a Gram positive bacterium, which causes neonatal invasive diseases as well as severe infections in the elderly and immune compromised patients. [1] On the basis of the capsular polysaccharide (CPS) structure, ten serotypes of GBS have been identified (Ia, Ib, II through IX). [2] Among these, type II GBS is one of the predominant GBS serotypes and responsible for 13% of early onset diseases. [3] Although the structure of GBS II was elucidated in 1983, [4] only one synthesis has been reported in literature. [5] The repeating unit of GBS type II is composed of α-Neu5Ac (2-3)-β-D-Gal-(1-4)-β-D-GlcNAc-(1-3)-[-β-D-Gal-(1-6)]-β-D Gal-(1-4)- β-D-Gal-(1-3)-β-D-Glc (Figure1).

In the present communication, we show our results of an novel approach to the synthesis of this heptasaccharide, based on the subcomponents highlighted in Figure 1. Suitably protected lactosamine C and lactose derivatives B are pivotal building blocks in our synthesis. [6] The synthetic GBS II fragments will be used for glycan array and structural studies and immunochemical characterization with specific monoclonal antibodies.

Figure 1. Structure and retrosynthetic fragmentation of GBS type II.

Nuccitelli A.; Rinaudo C. D.; Maione, D., Ther. Adv. Vaccines, 2015, 3(3), 76-90.

Cieslewicz, M. J.; Chaffin, D.; Glusman, G.; Kasper, D.; Madan, A.; Rodrigues, S.; Fahey, J.; Wessels, M. R.; and Rubens, C. E., Infection and Immunity, 2005, 73(5), 3096-3103.

Heath P. T., Vaccine, 2016, 34, 2876–2879.

Jennings, H. J.; Rosell, K. G.; Katzenellenbogen, E.; and Kasper, D. L., J. Biol. Chem., 1983, 258, 1793-1798.

Liming S., Han Z., Yaoyao L, Guofeng G, Feng C., Zhongwu G., and Jian G., J. Org. Chem.,2018, 83, 5920−5930.

This project has received funding from the H2020-MSCA-ITN-2015 “Glycovax’’ under grant agreement No 675671.

Contact eurocarb@eurocarb2019.com for general questions about EUROCARB2019, or codee@eurocarb2019.com for scientific questions.

Leiden University / Leiden Institute of Chemistry lic.leidenuniv.nl

European Carbohydrate Organisation

Congress by Design www.congressbydesign.com