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Tryptophan-based peptides grafted onto oxidized nanocellulose

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Abstract

Oxidized nanocellulose (ONC) have been synthesized and grafted with tryptophan-based peptides of varying lengths using a two step coupling method. The ONC was first activated by N-ethyl-N′-(3-dimethylaminopropyl) carbodiimide hydrochloride, forming a stable active ester in the presence of N-hydroxysuccinimide. Then, the active ester was reacted with the amino groups of the peptide forming an amide bond between ONC and peptide. Using this method, the intermolecular connection of Trp-based peptides (Trp-Ps) was avoided and uniform coupling of peptides on ONC was achieved. The coupling reaction was very fast in mild conditions and without alteration of the polysaccharide. The obtained products (ONC-Trp-Ps) were characterized by transmission electron microscopy and by different spectroscopic techniques.

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References

  • Ahmed A, Adnot A, Granmaison JL, Kaliaguine S, Doucet J (1987) ESCA analysis of cellulosic materials. Cellulose Chem Technol 21:483–492

    CAS  Google Scholar 

  • Albani JR (2007) Fluorescence spectroscopy principles. In: Principles and applications of fluorescence spectroscopy. Blackwell, Oxford, pp 88–113

  • Araki J, Wada M, Kuga S, Okano T (1998) Flow properties of microcrystalline cellulose suspension prepared by acid treatment of native cellulose. Colloids Surf A 142:75–82

    Article  CAS  Google Scholar 

  • Azizi Samir MAS, Alloin F, Dufresne A (2005) Review of recent research into cellulosic whiskers, their properties and their application in nanocomposite field. Biomacromolecules 6:612–626

    Article  Google Scholar 

  • Azzam F, Heux L, Putaux JL, Jean B (2010) Preparation by grafting onto, characterization, and properties of thermally responsive polymer-decorated cellulose nanocrystals. Biomacromolecules 11:3652–3659

    Article  CAS  Google Scholar 

  • Barazzouk S, Daneault C (2011) Spectroscopic characterization of oxidized nanocellulose grafted with fluorescent amino acids. Cellulose 18:643–653

    Article  CAS  Google Scholar 

  • Barry AO, Zoran Z (1990) Surface analysis by ESCA of sulfite post-treated CTMP. J Appl Polym Sci 39:31–42

    Article  CAS  Google Scholar 

  • Beck-Candanedo S, Roman M, Gray DG (2005) Effect of reaction conditions on the properties and behavior of wood cellulose nanocrystal suspensions. Biomacromolecules 6:1048–1054

    Article  CAS  Google Scholar 

  • Bondeson D, Mathew A, Oksman K (2006) Optimization of the isolation of nanocrystals from microcrystalline cellulose by acid hydrolysis. Cellulose 13:171–180

    Article  CAS  Google Scholar 

  • Bulpitt P, Aeschlimann D (1999) New strategy for chemical modification of hyaluronic acid: Preparation of functionalized derivatives and their use in the formation of novel biocompatible hydrogels. J Biomed Mater Res 47:152–169

    Article  CAS  Google Scholar 

  • Carr ME Jr, Hermans J (1978) Size and density of fibrin fibers from turbidity. Macromolecules 11:46–50

    Article  CAS  Google Scholar 

  • Chang PS, Robyt JF (1996) Oxidation of primary alcohol groups of naturally occurring polysacccharides with 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion. J Carbohydr Chem 15:819–830

    Article  CAS  Google Scholar 

  • Chanzy H (1990) Aspects of cellulose structure. In: Kennedy JF, Philips GO, William PA (eds) Cellulose sources and exploitation. Ellis Horwood Ltd., NY, pp 3–12

    Google Scholar 

  • Danishefsky I, Siskovic E (1971) Conversion of carboxyl groups of mucopolysaccharides into amides of amino acid esters. Carbohydr Res 16:199–205

    Article  CAS  Google Scholar 

  • de Nooy AE, Besemer AC, van Bekkum H (1995) Highly selective nitrosyl radical-mediated oxidation of primary alcohol groups in water-soluble glucans. Carbohydr Res 69:89–98

    Article  Google Scholar 

  • de Sousa Lima MM, Borsali R (2004) Rodlike cellulose microcrystals: structure, properties, and applications. Macromol Rapid Commun 25:771–787

    Article  Google Scholar 

  • Dieter-Klemm D, Schumann D, Kramer F, Hessler N, Koth D, Sultanova B (2009) Nanocellulose materials: different cellulose, different functionality. Macromol Symp 280:60–71

    Article  Google Scholar 

  • Dorris GM, Gray DG (1978) The surface analysis of paper and wood fibers by ESCA. Cellulose Chem Technol 12:9–23

    CAS  Google Scholar 

  • Elazzouzi-Hafraoui S, Nishiyama Y, Putaux JL, Heux L, Dubreuil F, Rochas C (2008) The shape and size distribution of crystalline nanoparticles prepared by acid hydrolysis of native cellulose. Biomacromol 9:57–65

    Article  CAS  Google Scholar 

  • Follain N, Montanari S, Jeacomine I, Gambarelli S, Vignon MR (2008) Coupling of amines with polyglucuronic acid: evidence for amide bond formation. Carbohydr Polym 74:333–343

    Article  CAS  Google Scholar 

  • Freire CSR, Silvestre AJD, Neto CP, Gandini A, Fardim P, Holmbom B (2006) Surface characterization by XPS, contact angle measurements and ToF-SIMS of cellulose fibers partially esterified with fatty acids. J Col Int Sci 301:205–209

    Article  CAS  Google Scholar 

  • Fujisawa S, Okita Y, Saito T, Togawa E, Isogai A (2011a) Formation of N-acylureas on the surface of TEMPO oxidizedcellulose nanofibril with carbodiimide in DMF. Cellulose 18:1191–1199

    Article  CAS  Google Scholar 

  • Fujisawa S, Okita Y, Fukuzumi H, Saito T, Isogai A (2011b) Preparation and characterization of TEMPO-oxidized cellulose nanofibril films with free carboxyl groups. Carbohydr Polym 84:579–583

    Article  CAS  Google Scholar 

  • Henriksson M, Berglund L (2007) Structure and properties of cellulose nanocomposite films containing melamine formaldehyde. J Appl Polym Sci 106:2817–2824

    Google Scholar 

  • Herrick FW, Casebier RL, Hamilton JK, Sandberg KR (1983) Microfibrillated cellulose: morphology and accessibility. J Appl Polym Sci Appl Polym Symp 37:797–805

    CAS  Google Scholar 

  • Hoare DG, Koshland DE Jr (1967) A method for the quantitative modification and estimation of carboxylic acid groups in proteins. J Biol Chem 242:2447–2453

    CAS  Google Scholar 

  • Hua X, Kaliaguine S, Kokta BV, Adnot A (1993) Surface analysis of explosion pulps by ESCA. Part 1. Carbon (1s) spectra and oxygen-to-carbon ratios. Wood Sci Technol 27:449–459

    Article  CAS  Google Scholar 

  • Isogai A, Kato Y (1998) Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation. Cellulose 5:153–164

    Article  CAS  Google Scholar 

  • Iwamoto S, Nakagaito AN, Yano H (2007) Nano-fibrillation of pulp fibers for the processing of transparent nanocomposites. Appl Phys A 89:461–466

    Google Scholar 

  • Jansen RJJ, Van Bekkum H (1995) XPS of nitrogen-containing functional groups on activated carbon. Carbon 33:1021–1027

    Article  CAS  Google Scholar 

  • Jiang K, Schadler LS, Siegel RW, Zhang X, Zhang H, Terrones M (2004) Protein immobilization on carbon nanotubes via a two-step process of diimide-activated amidation. J Mater Chem 14:37–39

    Article  CAS  Google Scholar 

  • Johansson LS, Campbell JM (2004) Reproducible XPS on biopolymers: cellulose studies. Surf Interface Anal 36:1018–1022

    Article  CAS  Google Scholar 

  • Kamdem DP, Riedl B, Adnot A, Kaliaguine S (1991) ESCA spectroscopy of poly(methylmethacrylate) grafted onto wood fibers. J Appl Polym Sci 43:1901–1912

    Article  CAS  Google Scholar 

  • Kamdem DP, Zhang J, Adnot A (2001) Identification of cupric and cuprous copper in copper naphthenate-treated wood by X-ray photoelectron spectroscopy. Holzforschung 55:16–20

    CAS  Google Scholar 

  • Klemm D, Heublein B, Fink HP, Bohn A (2005) Cellulose: fascinating biopolymer and sustainable raw material. Angew Chem Int Ed 44:3358–3393

    Article  CAS  Google Scholar 

  • Lasseuguette E (2008) Grafting onto microfibrils of native cellulose. Cellulose 15:571–580

    Article  CAS  Google Scholar 

  • Liu FPP, Rials TG, Simonsen J (1998) Relationship of wood surface energy to surface composition. Langmuir 14:536–541

    Article  CAS  Google Scholar 

  • Łojewska J, Miśkowiec P, Łojewski T, Proniewicz LM (2005) Cellulose oxidative and hydrolytic degradation: in situ FTIR approach. Polym Deg Stab 88:512–520

    Article  Google Scholar 

  • Matuana LM, Balatinecz JJ, Sodhi RNS, Park CB (2001) Surface characterization of esterified cellulosic fibers by XPS and FTIR spectroscopy. Wood Sci and Technol 35:191–201

    Article  CAS  Google Scholar 

  • Nzokou P, Kamdem DP (2005) X-ray photoelectron spectroscopy study of red oak-(Quercus rubra), black cherry—(Prunus serotina) and red pine—(Pinus resinosa) extracted wood surfaces. Surf Interf Anal 37:689–694

    Article  CAS  Google Scholar 

  • Oh SY, Yoo DI, Shin Y, Seo G (2005) FTIR analysis of cellulose treated with sodium hydroxide and carbon dioxide. Carbohydr Res 340:417–428

    Article  CAS  Google Scholar 

  • Olmstead JA, Gray DG (1997) Fluorescence spectroscopy of cellulose, lignin and mechanical pulps: a review. J Pulp Pap Sci 23:J571–J581

    CAS  Google Scholar 

  • Revol JF, Bradford H, Giasson J, Marchessault RH, Gray DG (1992) Helicoidal self-ordering of cellulose microfibrils in aqueous suspension. Int J Biol Macromol 14:170–172

    Article  CAS  Google Scholar 

  • Rzayev J, Hillmyer MA (2005) Nanochannel array plastics with tailored surface chemistry. J Am Chem Soc 127:13373–13379

    Article  CAS  Google Scholar 

  • Saito T, Isogai A (2005) Ion-exchange behavior of carboxylate groups in fibrous cellulose oxidized by the TEMPO-mediated system. Carbohydr Polym 61:183–190

    Article  CAS  Google Scholar 

  • Saito T, Shibata I, Isogai A, Suguri N, Sumikwa N (2005) Distribution of carboxylate groups introduced into cotton linters by the TEMPO-mediated oxidation. Carbohydr Polym 61:414–419

    Article  CAS  Google Scholar 

  • Saito T, Nishiyama Y, Putaux JL, Vignon M, Isogai A (2006) Homogeneous suspensions of individualized microfibrils from TEMPO-catalyzed oxidation of native cellulose. Biomacromol 7:1687–1691

    Article  CAS  Google Scholar 

  • Saito T, Kimura S, Nishiyama Y, Isogai A (2007) Cellulose nanofibers prepared by TEMPO-mediated oxidation of native cellulose. Biomacromol 8:2485–2491

    Article  CAS  Google Scholar 

  • Sugiyama J, Chanzy H, Revol JF (1994) On the polarity of cellulose in the cell wall of Valonia. Planta 193:260–265

    Article  CAS  Google Scholar 

  • Sun D, Zhou L, Wu Q, Yang S (2007) Preliminary research on structure and properties of nano-cellulose. J Wuhan Univ Tech Mater Sci Ed 22:677–680

    Article  CAS  Google Scholar 

  • Tahiri C, Vignon MR (2000) TEMPO-oxidation of cellulose: synthesis and characterization of polyglucuronans. Cellulose 7:177–188

    Article  CAS  Google Scholar 

  • Toner SD, Plitt KF (1962) Spectrofluorometric studies of degraded cotton cellulose. Tappi J 45:681–688

    CAS  Google Scholar 

  • Turbak AF, Snyder FW, Sandberg KR (1983) Microfibrillated cellulose, a new cellulose product: properties, uses, and commercial potential. J Appl Polym Sci Appl Polym Symp 37:815–827

    CAS  Google Scholar 

  • Zhang J, Elder TJ, Pu Y, Ragauskas AJ (2007) Facile synthesis of spherical cellulose nanoparticles. Carbohyd Polym 69:607–611

    Article  CAS  Google Scholar 

  • Zubavichus Y, Zharnikov M, Shaporenko A, Fuchs O, Weinhardt L, Heske C, Umbach E, Denlinger JD, Grunze M (2004) Soft X-ray induced decomposition of phenylalanine and tyrosine: a comparative study. J Phys Chem A 108:4557–4565

    Article  CAS  Google Scholar 

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Acknowledgments

The authors thank the Natural Sciences and Engineering Research Council of Canada for financial support of this work.

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  1. Centre de Recherche sur les Matériaux Lignocellulosiques, Université du Québec à Trois-Rivières, Trois-Rivières, QC, G9A 5H7, Canada

    Saïd Barazzouk & Claude Daneault

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  1. Saïd Barazzouk
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  2. Claude Daneault
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Correspondence to Saïd Barazzouk.

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Barazzouk, S., Daneault, C. Tryptophan-based peptides grafted onto oxidized nanocellulose. Cellulose 19, 481–493 (2012). https://doi.org/10.1007/s10570-011-9633-9

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