Towards the de novo synthesis of Pse; Total synthesis of P. aeruginosa strain 1244 pilin glycan

Professor Li, Xuechen   (Principal Investigator (PI))

36

2015-10-01

706972

Towards the de novo synthesis of Pse; Total synthesis of P. aeruginosa strain 1244 pilin glycan

bacterial glycan, chemical glycosylation, glycopeptide, total synthesis

Chemical Sciences

Physical Sciences (P)

17305615

General Research Fund (GRF)

2015

Completed

1 Develop a de novo synthesis of Pseudaminic acid (Pse). The easy access to this molecule would help address many fundamental questions of bacterial glycoproteins. 2 Study the chemical glycosylation of Pse. The diastereoselective glycosylation involving Pse has been reported to be very difficult. 3 Complete the total synthesis of P. aeruginosa 1244 pilin glycan-(alpha-5NβOHC4-7NFmPse-(2->4)-β-Xyl-(1->3)-β-FucNAc-β-Ser), which has not yet been reported. The presence of Pse and its β-linkage to xylose makes this synthesis very challenging. 4 Synthesize a glycopeptide containing alpha-5NβOHC4-7NFmPse-(2->4)-β-Xyl-(1->3)-β-FucNAc-β-Ser, which will lay the groundwork for synthesizing the full-length bacterial pilin glycoprotein (1-148).