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Title: Polypeptide Grafted Hyaluronan: Synthesis and Characterization

Abstract

Poly(L-leucine) grafted hyaluronan (HA-g-PLeu) has been synthesized via a Michael addition reaction between primary amine terminated poly(L-leucine) and acrylate-functionalized HA (TBAHA-acrylate). The precursor hyaluronan was first functionalized with acrylate groups by reaction with acryloyl chloride in the presence of triethylamine in N,N-dimethylformamide. 1H NMR analysis of the resulting product indicated that an increase in the concentration of acryloylchoride with respect to hydroxyl groups on HA has only a moderate effect on functionalization efficiency, f. A precise control of stoichiometry was not achieved, which could be attributed to partial solubility of intermolecular aggregates and the hygroscopic nature of HA. Michael addition at high [PLeu- NH2]/[acrylate]TBAHA ratios gave a molar grafting ratio of only 0.20 with respect to the repeat unit of HA, indicating grafting limitation due to insolubility of the grafted HA-g-PLeu. Soluble HA-g-PLeu graft copolymers were obtained for low grafting ratios (<0.039) with <8.6% by mass of PLeu and were characterized thoroughly using light scattering, 1H NMR, FT-IR, and AFM techniques. Light scattering experiments showed a strong hydrophobic interaction between PLeu chains, resulting in aggregates with segregated nongrafted HA segments. This yields local networks of aggregates, as demonstrated by atomic force microscopy. Circular dichroism spectroscopy showed a -sheet conformation formore » aggregates of poly(L-leucine).« less

Authors:
 [1];  [1];  [1];  [2]
  1. ORNL
  2. University of Tennessee, Knoxville (UTK)
Publication Date:
Research Org.:
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States); Center for Nanophase Materials Sciences
Sponsoring Org.:
USDOE Office of Science (SC)
OSTI Identifier:
990699
DOE Contract Number:  
DE-AC05-00OR22725
Resource Type:
Journal Article
Resource Relation:
Journal Name: Biomacromolecules; Journal Volume: 11; Journal Issue: 9
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; 59 BASIC BIOLOGICAL SCIENCES; 99 GENERAL AND MISCELLANEOUS//MATHEMATICS, COMPUTING, AND INFORMATION SCIENCE; HYALURONIC ACID; SYNTHESIS; CHEMICAL PROPERTIES; CHEMICAL ANALYSIS; DICHROISM; POLYPEPTIDES; PRECURSOR; SOLUBILITY; STOICHIOMETRY

Citation Formats

Wang, Xiaojun, Messman, Jamie M, Mays, Jimmy, and Baskaran, Durairaj. Polypeptide Grafted Hyaluronan: Synthesis and Characterization. United States: N. p., 2010. Web. doi:10.1021/bm1004146.
Wang, Xiaojun, Messman, Jamie M, Mays, Jimmy, & Baskaran, Durairaj. Polypeptide Grafted Hyaluronan: Synthesis and Characterization. United States. doi:10.1021/bm1004146.
Wang, Xiaojun, Messman, Jamie M, Mays, Jimmy, and Baskaran, Durairaj. Fri . "Polypeptide Grafted Hyaluronan: Synthesis and Characterization". United States. doi:10.1021/bm1004146.
@article{osti_990699,
title = {Polypeptide Grafted Hyaluronan: Synthesis and Characterization},
author = {Wang, Xiaojun and Messman, Jamie M and Mays, Jimmy and Baskaran, Durairaj},
abstractNote = {Poly(L-leucine) grafted hyaluronan (HA-g-PLeu) has been synthesized via a Michael addition reaction between primary amine terminated poly(L-leucine) and acrylate-functionalized HA (TBAHA-acrylate). The precursor hyaluronan was first functionalized with acrylate groups by reaction with acryloyl chloride in the presence of triethylamine in N,N-dimethylformamide. 1H NMR analysis of the resulting product indicated that an increase in the concentration of acryloylchoride with respect to hydroxyl groups on HA has only a moderate effect on functionalization efficiency, f. A precise control of stoichiometry was not achieved, which could be attributed to partial solubility of intermolecular aggregates and the hygroscopic nature of HA. Michael addition at high [PLeu- NH2]/[acrylate]TBAHA ratios gave a molar grafting ratio of only 0.20 with respect to the repeat unit of HA, indicating grafting limitation due to insolubility of the grafted HA-g-PLeu. Soluble HA-g-PLeu graft copolymers were obtained for low grafting ratios (<0.039) with <8.6% by mass of PLeu and were characterized thoroughly using light scattering, 1H NMR, FT-IR, and AFM techniques. Light scattering experiments showed a strong hydrophobic interaction between PLeu chains, resulting in aggregates with segregated nongrafted HA segments. This yields local networks of aggregates, as demonstrated by atomic force microscopy. Circular dichroism spectroscopy showed a -sheet conformation for aggregates of poly(L-leucine).},
doi = {10.1021/bm1004146},
journal = {Biomacromolecules},
number = 9,
volume = 11,
place = {United States},
year = {Fri Jan 01 00:00:00 EST 2010},
month = {Fri Jan 01 00:00:00 EST 2010}
}