Welcome to the new version of CaltechAUTHORS. Login is currently restricted to library staff. If you notice any issues, please email coda@library.caltech.edu
Published September 1994 | metadata_only
Journal Article

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


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.

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.

Additional details

August 20, 2023
August 20, 2023