Synthesis of a Polyurea from a Glucose- or Mannose-Containing N-Alkyl Urea Peptoid Oligomer

被引：42

作者：

Huang, Yongshun ^{[1
]}

Taylor, Leeanne ^{[1
]}

Chen, Xiaoping ^{[1
]}

Ayres, Neil ^{[1
]}

机构：

[1] Univ Cincinnati, Dept Chem, Cincinnati, OH 45221 USA

来源：

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY | 2013年 / 51卷 / 24期

基金：

美国国家科学基金会;

关键词：

biomaterials; biomimetic; step-growth polymerization; GLYCOSAMINOGLYCAN-MIMETIC BIOMATERIALS; ANTICOAGULANT ACTIVITY; HIGH-AFFINITY; HEPARIN; PENTASACCHARIDE; GLYCOPOLYMERS; FRAGMENT; SALT;

D O I：

10.1002/pola.26953

中图分类号：

O63 [高分子化学（高聚物）];

学科分类号：

070305 ; 080501 ; 081704 ;

摘要：

N-alkyl urea peptoid oligomers containing glucose or mannose have been synthesized and characterized. The oligomers were subsequently polymerized using a step-growth polymerization with hexamethylene diisocyanate. Equal moles of both monomers were used to guarantee high-molecular weight polymers. The polymers were characterized by gel permeation chromatography, nuclear magnetic resonance, and Fourier-transform infrared spectroscopy, and contact angle measurements of solvent cast thin films. Sulfation of the final polymers was achieved using a SO3/pyridine complex in pyridine to afford the heparin biomimetics. The average degree of sulfation was calculated to be 3.5 sulfates per saccharide as measured by elemental analysis. (c) 2013 Wiley Periodicals, Inc.

引用

页码：5230 / 5238

页数：9

共 44 条

[1] Synthesis and characterization of hyperbranched poly(urea-urethane)s based on AA* and B2B* monomers [J].

Abdelrehim, M ;

Komber, H ;

Langenwalter, J ;

Voit, B ;

Bruchmann, B .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2004, 42 (12) :3062-3081

[2] Synthesis and anticoagulant activity of sulfated glucoside-bearing polymer [J].

Akashi, M ;

Sakamoto, N ;

Suzuki, K ;

Kishida, A .

BIOCONJUGATE CHEMISTRY, 1996, 7 (04) :393-395

[3] Rotaxanes of cyclic peptides [J].

Aucagne, V ;

Leigh, DA ;

Lock, JS ;

Thomson, AR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) :1784-1785

[4] Polymer Brushes Containing Sulfonated Sugar Repeat Units: Synthesis, Charaderization, and In Vitro Testing of Blood Coagulation Activation [J].

Ayres, N. ;

Holt, D. J. ;

Jones, C. F. ;

Corum, L. E. ;

Grainger, D. W. .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2008, 46 (23) :7713-7724

[5] Glycosaminoglycan-mimetic biomaterials. 3. Glycopolymers prepared from alkene-derivatized mono- and disaccharide-based glycomonomers [J].

Baskaran, S ;

Grande, D ;

Sun, XL ;

Yayon, A ;

Chaikof, EL .

BIOCONJUGATE CHEMISTRY, 2002, 13 (06) :1309-1313

[6] Concepts for improved regioselective placement of O-sulfo, N-sulfo, N-acetyl, and N-carboxymethyl groups in chitosan derivatives [J].

Baumann, H ;

Faust, V .

CARBOHYDRATE RESEARCH, 2001, 331 (01) :43-57

[7] Observations on the structure of the barium salt of heparin [J].

Charles, AF ;

Todd, AR .

BIOCHEMICAL JOURNAL, 1940, 34 (01) :112-118

[8] Investigation into fiber formation in N-alkyl urea peptoid oligomers and the synthesis of a water-soluble PEG/N-alkyl urea peptoid oligomer conjugate [J].

Chen, Xiaoping ;

Ding, Keyang ;

Ayres, Neil .

POLYMER CHEMISTRY, 2011, 2 (11) :2635-2642

[9] Synthesis of Low Grafting Density Molecular Brush from a Poly(N-alkyl urea peptoid) Backbone [J].

Chen, Xiaoping ;

Ayres, Neil .

JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 2011, 49 (14) :3030-3037

[10] Synthesis of Novel Polymer/Urea Peptoid Conjugates Using RAFT Polymerization [J].

Chen, Xiaoping ;

Ayres, Neil .

MACROMOLECULES, 2010, 43 (03) :1341-1348

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