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Chemoenzymatic synthesis of novel N -(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films

2013; Wiley; Volume: 63; Issue: 8 Linguagem: Inglês

10.1002/pi.4660

1097-0126

Leandro N. Monsalve, Gabriela Petroselli, Rosa Erra-Ballsells, Analı́a Vázquez, Alicia Baldessari,

Carbohydrate Chemistry and Synthesis

Polymer InternationalVolume 63, Issue 8 p. 1523-1530 Research Article Chemoenzymatic synthesis of novel N-(2-hydroxyethyl)-β-peptoid oligomer derivatives and application to porous polycaprolactone films Leandro N. Monsalve, Corresponding Author Leandro N. Monsalve 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 INTI – Centro de Micro y Nanoelectrónica del Bicentenario, Parque tecnológico Miguelete, Av. General Paz 5445 (B1650WAB), San Martín, Buenos Aires, ArgentinaCorrespondence to: Leandro N. Monsalve, 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. E-mail: [email protected]Search for more papers by this authorGabriela Petroselli, Gabriela Petroselli 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, ArgentinaSearch for more papers by this authorRosa Erra-Ballsells, Rosa Erra-Ballsells 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, ArgentinaSearch for more papers by this authorAnalía Vázquez, Analía Vázquez 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, ArgentinaSearch for more papers by this authorAlicia Baldessari, Alicia Baldessari 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, ArgentinaSearch for more papers by this author Leandro N. Monsalve, Corresponding Author Leandro N. Monsalve 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 INTI – Centro de Micro y Nanoelectrónica del Bicentenario, Parque tecnológico Miguelete, Av. General Paz 5445 (B1650WAB), San Martín, Buenos Aires, ArgentinaCorrespondence to: Leandro N. Monsalve, 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. E-mail: [email protected]Search for more papers by this authorGabriela Petroselli, Gabriela Petroselli 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, ArgentinaSearch for more papers by this authorRosa Erra-Ballsells, Rosa Erra-Ballsells 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, ArgentinaSearch for more papers by this authorAnalía Vázquez, Analía Vázquez 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, ArgentinaSearch for more papers by this authorAlicia Baldessari, Alicia Baldessari 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, ArgentinaSearch for more papers by this author First published: 23 November 2013 https://doi.org/10.1002/pi.4660Citations: 7Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract 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 Supporting Information Filename Description pi4660-sup-0001-AppendixS1.docWord document, 1.9 MB Appendix S1. Supporting information pi4660-sup-0002-TableS1.docWord document, 39 KB Calculated and experimental m/z data for oligomer 2. pi4660-sup-0003-TableS2.docWord document, 29 KB C, H and N content of pristine PCL-80K, 2 and 4. pi4660-sup-0004-FigureS1.docWord document, 733.5 KB UV-MALDI-TOF spectrum of 2 performed in negative mode. Matrix: nHo. Labeled peaks are [M-H]. pi4660-sup-0005-FigureS2.docWord document, 290 KB FT-IR spectrum of oligomer 3. pi4660-sup-0006-FigureS3.docWord document, 258.5 KB FT-IR spectrum of 4. pi4660-sup-0007-FigureS4.docWord document, 171 KB GPC runs of 4 and pristine PCL-80K. Elution solvent: chloroform. pi4660-sup-0008-FigureS5.docWord document, 182 KB GPC run of 4 using UV detector (λ=254nm). Elution solvent: chloroform. pi4660-sup-0009-FigureS6.docWord document, 105.5 KB SEM micrographs of PCL films prepared with different amounts of 3 and 4. 3: 20% (a), 10% (b), 5% (c). 4: 20% (d), 10% (e), 5% (f). pi4660-sup-0010-FigureS7.docWord document, 160.5 KB Potentiometric titration curve of 2 with 0.1 N HCl. pH and |dpH/dV| were plotted against volume. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. 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