Solid Phase Synthesis of a Glycopeptide Analogue Using the Acid Sensitive 4-Methoxybenzhydryl Bromide Resin

Title: Solid Phase Synthesis of a Glycopeptide Analogue Using the Acid Sensitive 4-Methoxybenzhydryl Bromide Resin

Volume: 15 Issue: 1

Author(s): Theodore Tselios, Konstantinos Kelaidonis, Amalia Resvani, Konstantinos Prousalis, John Matsoukas and Theodore Tsegenidis

Affiliation:

Keywords: Glycopeptides, glycoproteins, 4-Methoxybenzhydryl bromide resin (MDMR-Br), Fmoc/tBu solid phase synthesis, glucosamine

Abstract: A convenient solid phase synthesis of a Thrombin Receptor Glycopeptide Mimetic analogue namely, 1-OMethyl- 2-N-{1’-(argininocarbonyl)-4’-[(4’’-fluoro)-benzylamido]-cyclohexane}-glucosamine using Fmoc/tBu methodology and the 4-Methoxybenzhydryl bromide resin is described. The synthesized analogue was purified by Reverse Phase High Performance Liquid Chromatography (RP-HPLC) and was identified by Electron Spray Ionization-Mass Spectrometry (ESI-MS) and Nuclear Magnetic Resonance (NMR). The synthetic protocol introduced for the first time successfully the acid sensitive 4-Methoxybenzhydryl bromide resin as a scaffold for the synthesis of glycopeptides resulting in high yield reactions. This synthetic procedure could be a general one for the convenient synthesis of such glyco compounds as the method was used for the first time to glycosylate a non peptide mimetic of an important protein sequence, in particular of the thrombin receptor active site S42FLLR46.

Cite this article as:

Tselios Theodore, Kelaidonis Konstantinos, Resvani Amalia, Prousalis Konstantinos, Matsoukas John and Tsegenidis Theodore, Solid Phase Synthesis of a Glycopeptide Analogue Using the Acid Sensitive 4-Methoxybenzhydryl Bromide Resin, Protein & Peptide Letters 2008; 15 (1) . https://dx.doi.org/10.2174/092986608783330323