Preparation, characterization, and application of poly(vinyl alcohol)-graft-poly(ethylene glycol) resins: novel polymer matrices for solid-phase synthesis.
Spherical crosslinked poly(vinyl alcohol) (PVA) beads with good mechanical stability were prepared by reverse-suspension polymerization, using dimethyl sulfoxide (DMSO) as a cosolvent in an aqueous phase. Poly(ethylene glycol)s with varying chain lengths were grafted onto the PVA beads by anionic polymerization of ethylene oxide. The thermal behavior, morphology, and swelling were evaluated for each of the new polymer matrices. High loading and good swelling in water and organic solvents were characteristic of the PEG-grafted PVA beads. The polymer beads also exhibited good mechanical and chemical stability and were unaffected by treatment with 6 N HCl and with 6 N NaOH. The hydroxyl groups of the PVA-PEG beads were converted into aldehyde, carboxylic acid, and isocyanate functions to provide scavenger resins and were extended by way of a benzyl alcohol in a Wang linker. The transglutaminase substrates dipeptides (Z-Gln-Gly) and heptapeptides (Pro-Asn-Pro-Gln-Leu-Pro-Phe) were synthesized on PVA-PEG_5, PVA-PEG_20, and the Wang linker-derivatized PVA-PEG resins. The cleavage of the peptides from the resins using MeOH/NH3 mixture at different temperatures (0 degrees C and room temp) and 50% TFA/DCM provided, respectively, peptide methyl esters, amides, and acids in good yields and purity as assessed by LC-MS analysis.
Luo
Juntao
J
Département de Chimie, Université de Montréal, C.P. 6128, Succursale Centre-ville, Montréal, QC, H3C 3J7 Canada.
Pardin
Christophe
C
Zhu
X X
XX
Lubell
William D
WD
D000447:Aldehydes / Q000737:chemistry; D000838:Anions / Q000737:chemistry; D002152:Calorimetry, Differential Scanning; D003432:Cross-Linking Reagents / Q000737:chemistry; D005027:Ethylene Oxide / Q000737:chemistry; D006900:Hydroxylation; D009682:Magnetic Resonance Spectroscopy; D008855:Microscopy, Electron, Scanning; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry; D011092:Polyethylene Glycols / Q000737:chemistry*; D011142:Polyvinyl Alcohol / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared
D000447:Aldehydes; D000838:Anions; D003432:Cross-Linking Reagents; D010455:Peptides; D011092:Polyethylene Glycols; D011142:Polyvinyl Alcohol; D005027:Ethylene Oxide