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

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

Journal Name: Protein & Peptide Letters

Volume 15 , Issue 1 , 2008

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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.

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

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Article Details

Year: 2008
Page: [1 - 5]
Pages: 5
DOI: 10.2174/092986608783330323

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