Bottom-up synthesis of hyaluronan and its derivatives via enzymatic polymerization: direct incorporation of an amido functional group.

Abstract:

:This paper reports the synthesis of hyaluronan (HA) and its derivatives via the hyaluronidase-catalyzed polymerization of 2-substituted oxazoline derivative monomers designed as "transition-state analogue substrates". Polymerization of 2-methyl oxazoline monomer from N-acetylhyalobiuronate (GlcAbeta(1-->3)GlcNAc) effectively proceeded at pH 7.5 and 30 degrees C, giving rise to synthetic HA (natural type) in an optimal yield of 78% via ring-opening polyaddition under total control of regioselectivity and stereochemistry. Hyaluronidase catalysis enabled the polymerization of 2-ethyl, 2-n-propyl, and 2-vinyl monomers, affording the corresponding HA derivatives (unnatural type) with N-propionyl, N-butyryl, and N-acryloyl functional groups, respectively, at the C2 position of all glucosamine units in good yields. The 2-isopropyl oxazoline derivative provided the N-isobutyryl derivative of HA in low yields. Monomers of 2-phenyl and 2-isopropenyl oxazoline derivatives were not polymerized. The mechanism of the polymerization is discussed.

journal_name

Biomacromolecules

journal_title

Biomacromolecules

authors

Ochiai H,Ohmae M,Mori T,Kobayashi S

doi

10.1021/bm049280r

keywords:

subject

Has Abstract

pub_date

2005-03-01 00:00:00

pages

1068-84

issue

2

eissn

1525-7797

issn

1526-4602

journal_volume

6

pub_type

杂志文章
  • In vitro studies of antifreeze glycoprotein (AFGP) and a C-linked AFGP analogue.

    abstract::Antifreeze glycoproteins (AFGPs) are a subclass of biological antifreezes found in deep sea Teleost fish. These compounds have the ability to depress the freezing point of the organism such that it can survive the subzero temperatures encountered in its environment. This physical property is very attractive for the cr...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm061044o

    authors: Liu S,Wang W,Moos Ev,Jackman J,Mealing G,Monette R,Ben RN

    更新日期:2007-05-01 00:00:00

  • Temperature-sensitive poly(vinyl alcohol)/poly(methacrylate-co-N-isopropyl acrylamide) microgels for doxorubicin delivery.

    abstract::Microgels based on poly(vinyl alcohol), PVA, grafted with methacrylate side chains, MA, incorporating N-isopropylacrylamide, NiPAAm, monomer, were prepared by water-in-water emulsion polymerization method. These systems exhibit a spherical shape and a volume-phase transition, that is, shrinking, below physiological te...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm900185u

    authors: Ghugare SV,Mozetic P,Paradossi G

    更新日期:2009-06-08 00:00:00

  • Synthesis, characterization, and pH-triggered dethreading of alpha-cyclodextrin-poly(ethylene glycol) polyrotaxanes bearing cleavable endcaps.

    abstract::The synthesis, characterization, and degradation kinetics of three alpha-cyclodextrin (alpha-CD)-poly(ethylene glycol) (PEG) polyrotaxanes with endcaps that were installed using Cu(I)-catalyzed Huisgen cyclization is reported. PEG1500, azidated with azidoacetic acid, was threaded with alpha-CD to form a pseudopolyrota...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm0602076

    authors: Loethen S,Ooya T,Choi HS,Yui N,Thompson DH

    更新日期:2006-09-01 00:00:00

  • Designing cell-aggregating peptides without cytotoxicity.

    abstract::We have designed α-helical peptides de novo that can induce aggregation of various kinds of cells by focusing on physicochemical properties such as hydrophobicity, net charges, and amphipathicity. It is shown that peptide hydrophobicity is the key factor to determine capabilities for cell aggregation while peptide net...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm4014414

    authors: Yamamoto N,Tamura A

    更新日期:2014-02-10 00:00:00

  • Well-defined homopolypeptides, copolypeptides, and hybrids of poly(l-proline).

    abstract::l-Proline is the only, out of 20 essential, amino acid that contains a cyclized substituted α-amino group (is formally an imino acid), which restricts its conformational shape. The synthesis of well-defined homo- and copolymers of l-proline has been plagued either by the low purity of the monomer or the inability of m...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm200495n

    authors: Gkikas M,Iatrou H,Thomaidis NS,Alexandridis P,Hadjichristidis N

    更新日期:2011-06-13 00:00:00

  • Self-Assembled Amphiphilic Starch Based Drug Delivery Platform: Synthesis, Preparation, and Interactions with Biological Barriers.

    abstract::Core-shell structured nanoparticles (NPs) render the simultaneous coloading capacity of both hydrophobic and hydrophilic drugs and may eventually enhance therapeutic efficacy. In this study, we employed a facile squalenoylation technology to synthesize a new amphiphilic starch derivative from partially oxidized starch...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c01430

    authors: Phan VHG,Trang Duong HT,Tran PT,Thambi T,Ho DK,Murgia X

    更新日期:2020-12-21 00:00:00

  • Synthesis and properties of degradable poly(urethane urea)s to be used for ligament reconstructions.

    abstract::In the present study we describe the synthesis, wet spinning, mechanical testing, and degradation of poly(urethane urea)s (PUURs) intended for clinical use in anterior cruciate ligament (ACL) reconstruction. The effects of soft segment chemical composition and molar mass and the kind of diamine chain extender on the m...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm025535u

    authors: Gisselfält K,Edberg B,Flodin P

    更新日期:2002-09-01 00:00:00

  • Synthesis and characterization of biocompatible thermo-responsive gelators based on ABA triblock copolymers.

    abstract::The synthesis of biocompatible, thermo-responsive ABA triblock copolymers in which the outer A blocks comprise poly(N-isopropylacrylamide) and the central B block is poly(2-methacryloyloxyethyl phosphorylcholine) is achieved using atom transfer radical polymerization with a commercially available bifunctional initiato...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm049331k

    authors: Li C,Tang Y,Armes SP,Morris CJ,Rose SF,Lloyd AW,Lewis AL

    更新日期:2005-03-01 00:00:00

  • Grafting of oligosaccharides onto synthetic polymer colloids.

    abstract::A new method to form colloidally stable oligosaccharide-grafted synthetic polymer particles has been developed. The oligosaccharides, of weight-average degree of polymerization approximately 38, were obtained by enzymatic debranching of amylopectin. Through the use of a cerium(IV)-based redox initiation process, oligo...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm061119o

    authors: Mange S,Dever C,De Bruyn H,Gaborieau M,Castignolles P,Gilbert RG

    更新日期:2007-06-01 00:00:00

  • Effects of PEGylation on membrane and lipopolysaccharide interactions of host defense peptides.

    abstract::Effects of poly(ethylene glycol) (PEG) conjugation on peptide interactions with lipid membranes and lipopolysaccharide (LPS) were investigated for KYE28 (KYEITTIHNLFRKLTHRLFRRNFGYTLR), an antimicrobial and anti-inflammatory peptide derived from human heparin cofactor II. In particular, effects of PEG length and locali...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm401884e

    authors: Singh S,Papareddy P,Mörgelin M,Schmidtchen A,Malmsten M

    更新日期:2014-04-14 00:00:00

  • Self-association of mucin.

    abstract::Aggregation phenomena in aqueous solutions of purified human tracheobronchial mucin have been studied by rheological methods, steady-state fluorescence, quasielastic light scattering, and spin probe techniques. At temperatures below 30 degrees C and concentrations above 15 mg/mL and in the absence of chaotropic agents...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm005532m

    authors: Bromberg LE,Barr DP

    更新日期:2000-10-01 00:00:00

  • Glyco-nanoparticles with sheddable saccharide shells: a unique and potent platform for hepatoma-targeting delivery of anticancer drugs.

    abstract::Reduction-sensitive shell-sheddable glyco-nanoparticles were designed and developed based on poly(ε-caprolactone)-graft-SS-lactobionic acid (PCL-g-SS-LBA) copolymer for efficient hepatoma-targeting delivery of doxorubicin (DOX). PCL-g-SS-LBA was prepared by ring-opening copolymerization of ε-caprolactone and pyridyl d...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm401749t

    authors: Chen W,Zou Y,Meng F,Cheng R,Deng C,Feijen J,Zhong Z

    更新日期:2014-03-10 00:00:00

  • Biologically Functionalized Expanded Polytetrafluoroethylene Blood Vessel Grafts.

    abstract::Cardiovascular diseases plague human health because of the lack of transplantable small-diameter blood vessel (SDBV) grafts. Although expanded polytetrafluoroethylene (ePTFE) has the potential to be used as a biocompatible material for SDBV grafts, long-term patency is still the biggest challenge. As discussed in this...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c00897

    authors: Wang D,Xu Y,Lin YJ,Yilmaz G,Zhang J,Schmidt G,Li Q,Thomson JA,Turng LS

    更新日期:2020-09-14 00:00:00

  • Self-Assembly of Cellulose in Super-Cooled Ionic Liquid under the Impact of Decelerated Antisolvent Infusion: An Approach toward Anisotropic Gels and Aerogels.

    abstract::Assembly of (bio)polymers into long-range anisotropic nanostructured gels and aerogels is of great interest in advanced material engineering since it enables directional tuning of properties, such as diffusivity, light, heat, and sound propagation, cell proliferation, and mechanical properties. Here we present an appr...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.8b01278

    authors: Plappert SF,Nedelec JM,Rennhofer H,Lichtenegger HC,Bernstorff S,Liebner FW

    更新日期:2018-11-12 00:00:00

  • Wheat germ agglutinin functionalized complexation hydrogels for oral insulin delivery.

    abstract::Insulin was loaded into hydrogel microparticles after two hours with loading efficiencies greater than 70% for both poly(methacrylic acid-grafted-ethylene glycol) (P(MAA-g-EG)) and poly(methacrylic acid-grafted-ethylene glycol) functionalized with wheat germ agglutinin (P(MAA-g-EG) WGA). The pH-responsive release resu...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm701274p

    authors: Wood KM,Stone GM,Peppas NA

    更新日期:2008-04-01 00:00:00

  • Improved stability and antidiabetic potential of insulin containing folic acid functionalized polymer stabilized multilayered liposomes following oral administration.

    abstract::The present study reports the folic acid (FA) functionalized insulin loaded stable liposomes with improved bioavailability following oral administration. Liposomes were stabilized by alternating coating of negatively charged poly(acrylic acid) (PAA) and positively charged poly(allyl amine) hydrochloride (PAH) over lip...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm401580k

    authors: Agrawal AK,Harde H,Thanki K,Jain S

    更新日期:2014-01-13 00:00:00

  • Endotoxin removing method based on lipopolysaccharide binding protein and polyhydroxyalkanoate binding protein PhaP.

    abstract::Polyhydroxyalkanoates (PHAs) granule associated protein PhaP has a strong affinity to PHA and other hydrophobic polymers. Human lipopolysaccharide binding protein (hLBP) is a natural endotoxin receptor in plasma. In this study, genes encoding hLBP fused with PhaP were expressed in Pichia pastoris GS115 for production ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm101230n

    authors: Li J,Shang G,You M,Peng S,Wang Z,Wu H,Chen GQ

    更新日期:2011-03-14 00:00:00

  • PLGA:poloxamer and PLGA:poloxamine blend nanoparticles: new carriers for gene delivery.

    abstract::The main objective of the present work was the development of new nanoparticulate carrier systems for the delivery of plasmid DNA. These new carriers consist of a blend matrix formed by a poly(lactic-co-glycolic acid) (PLGA) copolymer and polyoxyethylene derivatives. More specifically, we have prepared nanostructures ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm049577p

    authors: Csaba N,Caamaño P,Sánchez A,Domínguez F,Alonso MJ

    更新日期:2005-01-01 00:00:00

  • In vitro evaluation of textile chitosan scaffolds for tissue engineering using human bone marrow stromal cells.

    abstract::Textile chitosan fiber scaffolds were developed and tested in terms of biocompatibility for human bone marrow stromal cells (hBMSCs). A part of the scaffolds was further modified by coating with fibrillar collagen type I in order to biologize the surface. hBMSCs of two donors were used for cell culture experiments in ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm900172m

    authors: Heinemann C,Heinemann S,Lode A,Bernhardt A,Worch H,Hanke T

    更新日期:2009-05-11 00:00:00

  • A study of the chain stiffness and extension of alginates, in vitro epimerized alginates, and periodate-oxidized alginates using size-exclusion chromatography combined with light scattering and viscosity detectors.

    abstract::A series of alginates isolated from the stem and leaf of a brown algae (Laminaria hyperborea), bacterial mannuronan, in vitro epimerized mannuronans, and periodate oxidized alginates were analyzed by size-exclusion chromatography (SEC) combined with online multiangle laser light scattering (MALS) and viscometry (colle...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm060099n

    authors: Vold IM,Kristiansen KA,Christensen BE

    更新日期:2006-07-01 00:00:00

  • Modular Polymer Antigens To Optimize Immunity.

    abstract::Subunit vaccines can have excellent safety profiles, but their ability to give rise to robust immune responses is often compromised. For glycan-based vaccines, insufficient understanding of B and T cell epitope combinations that yield optimal immune activation hinders optimization. To determine which antigen features ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.9b01049

    authors: Bennett NR,Jarvis CM,Alam MM,Zwick DB,Olson JM,Nguyen HV,Johnson JA,Cook ME,Kiessling LL

    更新日期:2019-12-09 00:00:00

  • Aldehyde-Assisted Lignocellulose Fractionation Provides Unique Lignin Oligomers for the Design of Tunable Polyurethane Bioresins.

    abstract::Thanks to chemical stabilization, aldehyde-assisted fractionation (AAF) of lignocellulosic biomass has recently emerged as a powerful tool for the production of largely uncondensed lignin. Depolymerization of AAF lignin via ether cleavage provides aromatic monomers at near theoretical yields based on ether cleavage an...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.0c00927

    authors: Vendamme R,Behaghel de Bueren J,Gracia-Vitoria J,Isnard F,Mulunda MM,Ortiz P,Wadekar M,Vanbroekhoven K,Wegmann C,Buser R,Héroguel F,Luterbacher JS,Eevers W

    更新日期:2020-10-12 00:00:00

  • Noninvasive in vivo monitoring of the biofate of 195 kDa poly(vinyl alcohol) by multispectral fluorescence imaging.

    abstract::A comprehensive knowledge of the in vivo fate of polymers is essential for their potential application in humans. In this study, the body distribution, accumulation, and elimination processes of intraperitoneally (ip) administered poly(vinyl alcohol) (PVA) in mice were investigated in detail. Two derivatives of PVA (1...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm200899h

    authors: Schädlich A,Naolou T,Amado E,Schöps R,Kressler J,Mäder K

    更新日期:2011-10-10 00:00:00

  • Anticoagulant Heparin Mimetics via RAFT Polymerization.

    abstract::Heparin, a sulfated polysaccharide derived from animal sources, is the most commonly used parenteral anticoagulant drug, but it suffers from significant safety and supply issues. Herein, we describe the preparation of heparin mimetic homo- and copolymers via the reversible addition-fragmentation chain transfer (RAFT) ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.9b01688

    authors: Nahain AA,Ignjatovic V,Monagle P,Tsanaktsidis J,Vamvounis G,Ferro V

    更新日期:2020-02-10 00:00:00

  • Synthesis of multifunctional cellulose nanocrystals for lectin recognition and bacterial imaging.

    abstract::Multifunctional cellulose nanocrystals have been synthesized and applied as a new type of glyconanomaterial in lectin binding and bacterial imaging. The cellulose nanocrystals were prepared by TEMPO-mediated oxidation and acidic hydrolysis, followed by functionalization with a quinolone fluorophore and carbohydrate li...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.5b00227

    authors: Zhou J,Butchosa N,Jayawardena HS,Park J,Zhou Q,Yan M,Ramström O

    更新日期:2015-04-13 00:00:00

  • Cyclic Dipeptide-Based Ambidextrous Supergelators: Minimalistic Rational Design, Structure-Gelation Studies, and In Situ Hydrogelation.

    abstract::Ambidextrous supergelators are developed through structure-gelation screening of rationally designed cyclic dipeptides (CDPs). The organo- and hydrogels of CDPs were thoroughly characterized by their minimal gelation concentration (MGC) for organic and aqueous solvents, thermal stability (Tg), and viscoelastic propert...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.7b00924

    authors: Manchineella S,Murugan NA,Govindaraju T

    更新日期:2017-11-13 00:00:00

  • Preserving catalytic activity and enhancing biochemical stability of the therapeutic enzyme asparaginase by biocompatible multilayered polyelectrolyte microcapsules.

    abstract::The present study focuses on the formation of microcapsules containing catalytically active L-asparaginase (L-ASNase), a protein drug of high value in antileukemic therapy. We make use of the layer-by-layer (LbL) technique to coat protein-loaded calcium carbonate (CaCO3) particles with two or three poly dextran/poly-L...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm401341k

    authors: Karamitros CS,Yashchenok AM,Möhwald H,Skirtach AG,Konrad M

    更新日期:2013-12-09 00:00:00

  • Kinetics of protein-protein complex coacervation and biphasic release of salbutamol sulfate from coacervate matrix.

    abstract::Turbidimetric titration was used to initiate associative intermolecular interactions between a pair of protein molecules, gelatin-A and gelatin-B, having complementary charges that led to pH-induced liquid-liquid phase separation and the formation of complex coacervate. The stoichiometric binding ratio was found to be...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm801160s

    authors: Tiwari A,Bindal S,Bohidar HB

    更新日期:2009-01-12 00:00:00

  • Preparation of Dental Resins Resistant to Enzymatic and Hydrolytic Degradation in Oral Environments.

    abstract::The short average service life of traditional dental composite restorative materials and increasing occurrence of secondary caries adjacent to composite restorations and sealants are necessitating the development of new, longer lasting compositions. Novel monomers and their polymers, reinforcing fillers, and adhesive ...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/acs.biomac.5b01069

    authors: Gonzalez-Bonet A,Kaufman G,Yang Y,Wong C,Jackson A,Huyang G,Bowen R,Sun J

    更新日期:2015-10-12 00:00:00

  • Molecular orientation distributions in a biaxially oriented poly(L-lactic acid) film determined by polarized Raman spectroscopy.

    abstract::Molecular orientation distributions in the crystalline and amorphous regions of a biaxially oriented poly(L-lactic acid) film were analyzed fully by polarized Raman spectroscopy. Raman bands at 926 and 875 cm(-1) were chosen for the determination of the most probable molecular orientation distribution functions for th...

    journal_title:Biomacromolecules

    pub_type: 杂志文章

    doi:10.1021/bm060326l

    authors: Tanaka M,Young RJ

    更新日期:2006-09-01 00:00:00