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Abstract:

The biocatalytic synthesis of a novel peptoid oligomer is reported. The oligomer is acetylated and a copolymer with polycaprolactone is prepared. These derivatives are employed for the preparation of nanoporous films. Poly[N-(2-hydroxyethyl)-β-propylamide] oligomer is synthesized using a simple enzymatic procedure involving Candida antarctica lipase B. This novel compound is obtained by a green and chemoselective method from economic reactants in good yield. The β-peptoid oligomer is characterized by spectroscopic methods showing low molecular weight and low dispersity. Two derivatives of the β-peptoid oligomer are prepared by acetylation and by grafting polycaprolactone by ring opening polymerization from the pendant hydroxyl groups. These products are blended with polycaprolactone to make films by solvent casting. The inclusion of the acyl derivatives of the β-peptoid to polycaprolactone affects the morphology of the film yielding microstructured and nanostructured patterns. © 2013 Society of Chemical Industry.

Registro:

Documento: Artículo
Título:Chemoenzymatic synthesis of novel N-(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films
Autor:Monsalve, L.N.; Petroselli, G.; Erra-Ballsells, R.; Vázquez, A.; Baldessari, A.
Filiación:Laboratorio de Polímeros y Materiales Compuestos, Instituto de Tecnología en Polímeros y Nanotecnología (ITPN), Facultad de Ingeniería, UBA - CONICET, Las Heras 2214 (C1127AAR), Buenos Aires, Argentina
Departamento de Química Orgánica y CIHIDECAR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Piso 3 (C1428EGA), Buenos Aires, Argentina
INTI - Centro de Micro y Nanoelectrónica del Bicentenario, Parque tecnológico Miguelete, Av. General Paz 5445 (B1650WAB), Buenos Aires, Argentina
Laboratorio de Biocatálisis, Departamento de Química Orgánica y UMYMFOR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Piso 3 (C1428EGA), Buenos Aires, Argentina
Palabras clave:Films; Lipase; Polycaprolactone; Surface properties; β-peptoid; Acetylation; Films; Lipases; Oligomers; Polycaprolactone; Ring opening polymerization; Spectroscopic analysis; Surface properties; Biocatalytic synthesis; Candida antarctica lipase; Chemo-enzymatic synthesis; Chemoselective methods; Low molecular weight; Peptoid; Polycaprolactone films; Spectroscopic method; Film preparation
Año:2014
Volumen:63
Número:8
Página de inicio:1523
Página de fin:1530
DOI: http://dx.doi.org/10.1002/pi.4660
Título revista:Polymer International
Título revista abreviado:Polym. Int.
ISSN:09598103
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09598103_v63_n8_p1523_Monsalve

Referencias:

  • Inamura, I., Watanabe, N., Umezawa, N., Iwatsubo, T., Kato, N., Tomita, T., (2009) J Am Chem Soc, 131, pp. 7353-7359
  • Xue, Y., Tang, X., Huang, J., Zhang, X., Yu, J., Shang, Y., (2011) Colloids Surf B, 85, pp. 280-288
  • Godballe, T., Nilsson, L.L., Petersen, P.D., Jenssen, H., (2011) Chem Biol Drug Des, 77, pp. 107-116
  • Zuckerman, F.N., Kerr, H.M., Kent, S.B.H., Moos, W.H., (1992) J Am Chem Soc, 114, pp. 10646-10647
  • Zhang, D., Lahasky, H., Guo, L., Lee, C.-U., Lavan, M., (2012) Macromolecules, 45, pp. 5833-5841
  • Cheng, J., Deming, T.J., (2001) J Am Chem Soc, 123, pp. 9457-9458
  • Schwab, L.W., Kroon, R., Schouten, A.J., Loos, K., (2008) Macromol Rapid Commun, 29, pp. 794-797
  • Cheng, J., Deming, T.J., (2001) Macromolecules, 34, pp. 5169-5174
  • Grossmann, A., Luxenhofer, R., (2012) Macromol Rapid Commun, 33, pp. 1714-1719
  • Lin, S., Yu, X., Tu, Y., Xu, H., Cheng, S.Z.D., Jia, L., (2010) Chem Commun, 46, pp. 4273-4275
  • Jia, L., Sun, H., Shay, T., Allgeier, A.M., Hanton, S.D., (2002) J Am Chem Soc, 124, pp. 7282-7283
  • Hamper, B.C., Kolodziej, S.A., Sactes, A.M., Smith, R.G., Cortez, E., (1998) J Org Chem, 63, pp. 708-718
  • Kobayashi, S., (2010) Proc Jpn Acad Ser B, 86, pp. 338-365
  • Poojari, Y., Clarson, S.J., (2010) Macromolecules, 43, pp. 4616-4622
  • Monsalve, L.N., Fatema, M.K., Nonami, H., Erra-Balsells, R., Baldessari, A., (2010) Polymer, 51, pp. 2998-3005
  • Rustoy, E.M., Sato, Y., Nonami, H., Erra-Balsells, R., Baldessari, A., (2007) Polymer, 48, pp. 1517-1525
  • Monsalve, L.N., Gillanders, F., Baldesari, A., (2012) Eur J Polym Chem, 2012, pp. 1164-1170
  • Ulery, B.D., Nair, L.S., Laurencin, C.T., (2011) J Polym Sci B Polym Phys, 49, pp. 832-864
  • Plackett, D.V., Holm, V.K., Johansen, P., Ndoni, S., Nielsen, P.V., Sipilainen-Malm, T., (2006) Packag Technol Sci, 19, pp. 1-24
  • Li, S.M., Chen, X.H., Gross, R.A., McCarthy, S.P., (2000) J Mater Sci Mater Med, 11, pp. 227-233
  • Zhu, Y., Gao, C., Liu, X., Shen, H., (2002) Biomacromolecules, 3, pp. 1312-1319
  • Ludueña, L.N., Álvarez, V., Vázquez, A., (2007) Mater Sci Eng A, 460 (1), pp. 121-129
  • Lönnberg, H., Fogelström, L., Zhou, Q., Hult, A., Berglund, L., Malmström, E., (2011) Compos Sci Technol, 71, pp. 9-12
  • Martino, V.P., Pollet, E., Avérous, L.J., (2011) Polym Environ, 19, pp. 819-826
  • Sharifi, S., Shafieyan, Y., Mirzadeh, H., Bagheri-Khoulenjani, S., Rabiee, S.M., Imani, M., (2011) J Biomed Mater Res A, 98, pp. 257-267
  • Mangiacapra, P., Raimondo, M., Tammaro, L., Vittoria, V., Malinconico, M., Laurienzo, P., (2007) Biomacromolecules, 8, pp. 773-779
  • Miao, Z.M., Cheng, S.X., Zhang, X.Z., Zhuo, R.X., (2005) Biomacromolecules, 6, pp. 3449-3457
  • Yuan, C., Lu, H.C., Li, Q.Z., Yang, S., Zhao, Q.L., Huang, J., (2012) J Polym Sci A Polym Chem, 50, pp. 2398-2405
  • Ku, S.H., Lee, S.H., Parck, C.B., (2012) Biomaterials, 33, pp. 6098-6104
  • Ogata, N., Asahara, T., (1966) Bull Chem Soc Jpn, 39, pp. 1486-1490
  • Person, P.V., Casas, J., Iversen, T., Córdova, A., (2006) Macromolecules, 39, pp. 2819-2822. , DOI 10.1021/ma0521710
  • Domínguez de María, P., (2010) Chem Cat Chem, 2, pp. 487-492
  • Massard, C., Bernard, L., Cueff, R., Raspal, V., Feschet-Chassot, E., Sibaud, Y., (2012) Prog Org Coat, 75, pp. 116-123
  • Cai, Y.F., Li, L., Luo, M.X., Yang, K.F., Lai, G.Q., Jiang, J.X., (2011) Chirality, 23, pp. 397-403
  • Liu, L., Li, S., Garreau, H., Vert, M., (2000) Biomacromolecules, 1, pp. 350-359
  • Wang, K., Cai, L., Jesse, S., Wang, S., (2012) Langmuir, 28, pp. 4382-4395
  • Rosales, A.M., Murnen, H.K., Zuckermann, R.N., Segalman, R.A., (2010) Macromolecules, 43, pp. 5627-5636
  • Jianwei, M.J., Sun, Y., Gelichauf, K., Lou, J., Li, Q., (2011) Langmuir, 27, pp. 10035-10040
  • Mishra, A., Das Purkayastha, B.P., Roy, J.K., Aswal, V.K., Maiti, P., (2010) Macromolecules, 43, pp. 9928-9936
  • Wan, L.H., Li, Q.L., Chen, P.C., Xu, Z.K., (2012) Chem Commun, 48, pp. 4417-4419

Citas:

---------- APA ----------
Monsalve, L.N., Petroselli, G., Erra-Ballsells, R., Vázquez, A. & Baldessari, A. (2014) . Chemoenzymatic synthesis of novel N-(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films. Polymer International, 63(8), 1523-1530.
http://dx.doi.org/10.1002/pi.4660
---------- CHICAGO ----------
Monsalve, L.N., Petroselli, G., Erra-Ballsells, R., Vázquez, A., Baldessari, A. "Chemoenzymatic synthesis of novel N-(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films" . Polymer International 63, no. 8 (2014) : 1523-1530.
http://dx.doi.org/10.1002/pi.4660
---------- MLA ----------
Monsalve, L.N., Petroselli, G., Erra-Ballsells, R., Vázquez, A., Baldessari, A. "Chemoenzymatic synthesis of novel N-(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films" . Polymer International, vol. 63, no. 8, 2014, pp. 1523-1530.
http://dx.doi.org/10.1002/pi.4660
---------- VANCOUVER ----------
Monsalve, L.N., Petroselli, G., Erra-Ballsells, R., Vázquez, A., Baldessari, A. Chemoenzymatic synthesis of novel N-(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films. Polym. Int. 2014;63(8):1523-1530.
http://dx.doi.org/10.1002/pi.4660