Jörg Habermann

Solid-phase synthesis of a glycopeptide from the homophilic recognition domain of epithelial cadherin 1 using a O-pentafluorophenyluronium salt

Abstract The β-turn forming glycopeptide 6 from the homophilic recognition domain of mouse epithelial cadherin 1 carrying a T N -antigen side chain was synthesised on solid phase using an allylic anchor and the new coupling reagent N , N - N ′, N ′-bis(tetramethylene)- O -pentafluorophenyluronium hexafluorophosphate 3 .

Fragment condensation on solid-phase in the synthesis of an amphiphilic glycopeptide from the homophilic recognition domain of epithelial cadherin 1

Abstract The lipo-glycopeptide 6 containing the homophilic recognition motif of mouse epithelial cadherin 1 was synthesised via a fragment condensation on a solid phase linked peptide using an allylic anchor and a pentafluorophenol-based coupling reagent.

Clean synthesis of α-bromo ketones and their utilisation in the synthesis of 2-alkoxy-2,3-dihydro-2-aryl-1,4-benzodioxanes, 2-amino-4-aryl-1,3-thiazoles and piperidino-2-amino-1,3-thiazoles using polymer-supported reagents

An array of 2-alkoxy-2,3-dihydro-2-aryl-1,4-benzodioxane derivatives and 2-amino-1,3-thiazoles were prepared in high yield using a straightforward three-step and two- step sequence of polymer-supported reagents, respectively and other polymer-supported sequestering reagents without any chromatographic purification step. A key step involves clean and efficient bromination of acetophenones using polymer-supported pyridinium bromide perbromide (PSPBP) and subsequent cyclisation reaction.

Chemistry of glycopeptides

For a long time, peptides and proteins on the one hand and carbohydrates on the other have been considered separate classes of natural products. The rather strict distinction between these major fields of natural product chemistry is still apparent not only in the organisation of chemistry text books but also in the different approaches to immunological and cell biological recognition phenomena.