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Trifluoroalanine N-Carboxy Anhydride: A Reactive Intermediate for the Synthesis of Low Surface Energy Polypeptides

Dessipri, E. and Tirrell, D. A. (1994) Trifluoroalanine N-Carboxy Anhydride: A Reactive Intermediate for the Synthesis of Low Surface Energy Polypeptides. Macromolecules, 27 (19). pp. 5463-5470. ISSN 0024-9297. https://resolver.caltech.edu/CaltechAUTHORS:DESm1994

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Abstract

D,L-Trifluoroalanine N-carboxy anhydride (D,L-TFANCA) was synthesized by phosgenation of 3,3,3-D,L-trifluoroalanine in tetrahydrofuran. ^1H nuclear magnetic resonance and infrared spectra indicate that the electron withdrawing trifluoromethyl group in the a position increases the acidity of the amide proton and the electrophilicity of the carbonyl groups of the anhydride. D,L-TFANCA was polymerized with aniline, thiophenol, or triethylamine as initiator. Time of flight matrix assisted laser desorption mass spectrometry was used to determine the absolute molecular weights and molecular weight distributions of the resulting polypeptides. Knowledge of the exact molecular weight confirmed the structural integrity of the products and gave insight into the mechanism of polymerization. D,L-TFANCA was also copolymerized with γ-benzyl L-glutamate NCA. Incorporation of 20 mol % D,L-trifluorodanine into poly(γ-benzyl L-glutamate) leads to a marked decrease in the surface energy of the polymer, as determined by contact angle measurements.


Item Type:Article
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URLURL TypeDescription
http://dx.doi.org/10.1021/ma00097a028DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ma00097a028PublisherArticle
ORCID:
AuthorORCID
Tirrell, D. A.0000-0003-3175-4596
Additional Information:© 1994 American Chemical Society. Received April 1, 1994; Revised Manuscript Received June 22, 1994. The TOF-MALD mass spectra were acquired at Millipore Corp. by Dr. Denis Michaud, whose time and effort are deeply appreciated. We also wish to acknowledge Jacob Hirsch for acquiring the XPS data. This work was supported by grants from the NSF Materials Research Laboratory at the University of Massachusetts and from the US. Army Research Office.
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NSFUNSPECIFIED
Army Research Office (ARO)UNSPECIFIED
Issue or Number:19
Record Number:CaltechAUTHORS:DESm1994
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:DESm1994
Official Citation:Trifluoroalanine N-Carboxy Anhydride: A Reactive Intermediate for the Synthesis of Low Surface Energy Polypeptides E. Dessipri and D. A. Tirrell Macromolecules 1994 27 (19), 5463-5470
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:53490
Collection:CaltechAUTHORS
Deposited By: Anne Hormann
Deposited On:27 Jan 2015 17:40
Last Modified:03 Oct 2019 07:50

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