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Antigens derived from the mucin MUC1 [Elektronisk resurs] Solution and solid-phase synthesis of saccharides, peptides and glycopeptides

Pudelko, Maciej, 1978- (författare)
Elofsson, Mikael (preses)
Almqvist, Fredrik (preses)
Lindhorst, Thisbe K. (opponent)
Umeå universitet Teknisk-naturvetenskaplig fakultet (utgivare)
Publicerad: Umeå : Kemi, 2008
Engelska 76
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  • E-bokAvhandling(Diss. (sammanfattning) Umeå : Umeå universitet, 2008)
Sammanfattning Ämnesord
  • Mucin is a term used to describe a large family of heavily glycosylated proteins which are present on the surfaces of secretory epithelial cells and are overexpressed by many carcinomas. Membrane-bound mucin MUC1 is of special interest. Its backbone consists of repeating units of twenty amino acids with five potential glycosylation sites. These sites are expanded to structures like the T (Gal β (1->3)GalNA cα -Ser/Thr) and T n (GalNA cα -Ser/Thr) antigens by the action of various glycosyltransferases. In different types of carcinomas these epitopes are being terminated by sialic acid residues to form among others: 2,3-sialyl- T and sialyl- T n structures due to the elevated levels of different sialyltransferases. Solid-phase synthesis of the selected antigens derived from the mucin MUC1 has been developed and optimized. A chemoenzymatic approach has been used to effectively prepare 2,3-sialyl- T and 2,6-sialyl- T n glycopeptides. The formation of intramolecular sialic acid lactones in presence of acetic acid was investigated. The stability of lactones formed from 2,3-sialyl- T towards water was studied using NMR spectroscopy and it appeared that 1''->2' lactone displayed remarkable strength to hydrolysis and it was suggested as a candidate for cancer vaccine. Gel-phase 19 F NMR spectroscopy is known to be a very good tool to characterize resin-bound products using fluorinated protecting groups and linker molecules. The hydrophobic peptide LLLLTVLTV, which is a fragment from the MUC1 signal sequence, was prepared using solid-phase synthesis according to a modified Fmoc protocol with more active coupling reagent, stronger base, and the isopropylidene dipeptide Fmoc-Leu-Thr-(Ψ Me,Me pro)-OH. Gel-phase 19 F NMR spectroscopy was used to evaluate peptide chain aggregation and coupling and deprotection efficiency. A carbamate linker strategy proved to be effective in solid-phase synthesis of serine-based neoglycolipids with terminal amino functionality. Neoglycolipids were covalently bound to secondary amines in microtiter plates using squaric acid ester methodology. These arrays have potential to study the interactions between carbohydrates and e.g. proteins and microbes. The new fluorinated α -amino protective group [1-(4-(4-fluorophenyl)-2,6-dioxocyclohexylidene)ethyl] Fde was developed. This group is cleaved with hydrazine in DMF solution. By using amino acids protected with this group, it was possible to quantify the efficiency of peptide coupling using gel-phase 19 F NMR spectroscopy. 


Natural Sciences  (hsv)
Chemical Sciences  (hsv)
Organic Chemistry  (hsv)
Naturvetenskap  (hsv)
Kemi  (hsv)
Organisk kemi  (hsv)
Chemistry  (svep)
Organic chemistry  (svep)
Kemi  (svep)
Organisk kemi  (svep)


government publication  (marcgt)

Indexterm och SAB-rubrik

signal peptide
neoglycolipid arrays
solid-phase synthesis
gel-phase 19F NMR spectroscopy
fluorinated alpha-amino protective group
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