Solid phase synthesis of a glycopeptide analogue using the acid sensitive 4-methoxybenzhydryl bromide resin.
A convenient solid phase synthesis of a Thrombin Receptor Glycopeptide Mimetic analogue namely, 1-O-Methyl-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.
Tselios
Theodore
T
Department of Chemistry, University of Patras, 26500 Patras, Greece. ttselios@upatras.gr
Kelaidonis
Konstantinos
K
Resvani
Amalia
A
Prousalis
Konstantinos
K
Matsoukas
John
J
Tsegenidis
Theodore
T
D001665:Binding Sites; D002851:Chromatography, High Pressure Liquid; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D018716:Molecular Mimicry; D018179:Receptors, Thrombin / Q000737:chemistry; D012117:Resins, Synthetic; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods
C528627:1-O-methyl-2-N-(1'-(argininocarbonyl)-4'-((4''-fluoro)benzylamido)cyclohexane)glucosamine; D006020:Glycopeptides; D018179:Receptors, Thrombin; D012117:Resins, Synthetic