Synthesis of a novel polyurethane co-polymer containing covalently attached RGD peptide.
The synthesis of a novel polyurethane block co-polymer containing a covalently attached, well-oriented RGD (Arg-Gly-Asp) peptide was explored. A poly(tetramethylene oxide) (PTMO)-based polyurethane was synthesized, and a bimolecular nucleophilic substitution reaction was then employed to incorporate ethyl carboxylate groups onto the polymer backbone (i.e. carboxylated polyurethane). Elemental analysis was used to determine the extent of carboxylation. The hexapeptide H-Gly-Arg-Gly-Asp-Ser-Tyr-OH was coupled to the carboxylated polyurethane via the formation of an amide bond. The attachment of the peptide was controlled by a protection-deprotection scheme. Nuclear magnetic resonance (NMR) and Fourier transform infrared (FTIR) spectroscopies were used to monitor the reactions. Sakaguchi assay and amino acid analysis confirmed that the RGD-containing peptide was successfully grafted onto the carboxylated polyurethane. This reaction scheme provides a new route for grafting end-linked, bioactive peptides onto polyurethanes.
Lin
H B
HB
Department of Chemical Engineering, University of Wisconsin-Madison 53706.
Zhao
Z C
ZC
Garcia-Echeverria
C
C
Rich
D H
DH
Cooper
S L
SL
D000595:Amino Acid Sequence; D001120:Arginine / Q000032:analysis; D002264:Carboxylic Acids / Q000737:chemistry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis*; D011140:Polyurethanes / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D009626:Terminology as Topic
D002264:Carboxylic Acids; D009842:Oligopeptides; D011140:Polyurethanes; C075325:glycyl-arginyl-glycyl-aspartyl-seryl-tyrosine; C047981:arginyl-glycyl-aspartic acid; D001120:Arginine