Hydrolytic Stability of Hydrazones and Oximes

Angewandte Chemie International EditionVolume 47, Issue 39 p. 7523-7526 Communication Hydrolytic Stability of Hydrazones and Oximes† Jeet Kalia, Jeet Kalia Department of Biochemistry, University of Wisconsin-Madison, 433 Babcock Drive, Madison, WI 53706-1544 (USA), Fax: (+1) 608-262-3453 http://www2.biochem.wisc.edu/rainesSearch for more papers by this authorRonald T. Raines Prof., Ronald T. Raines Prof. [email protected] Department of Biochemistry, University of Wisconsin-Madison, 433 Babcock Drive, Madison, WI 53706-1544 (USA), Fax: (+1) 608-262-3453 http://www2.biochem.wisc.edu/raines Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706-1322 (USA)Search for more papers by this author Jeet Kalia, Jeet Kalia Department of Biochemistry, University of Wisconsin-Madison, 433 Babcock Drive, Madison, WI 53706-1544 (USA), Fax: (+1) 608-262-3453 http://www2.biochem.wisc.edu/rainesSearch for more papers by this authorRonald T. Raines Prof., Ronald T. Raines Prof. [email protected] Department of Biochemistry, University of Wisconsin-Madison, 433 Babcock Drive, Madison, WI 53706-1544 (USA), Fax: (+1) 608-262-3453 http://www2.biochem.wisc.edu/raines Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI 53706-1322 (USA)Search for more papers by this author First published: 09 September 2008 https://doi.org/10.1002/anie.200802651Citations: 637 † We are grateful to Prof. W. W. Cleland, Prof. S. F. Nelsen, M. D. Shoulders, and T. J. Rutkoski for contributive discussions, and Dr. C. G. Fry for providing laboratory space and unconstrained access to NMR spectrometers in the Department of Chemistry. This work was supported by NIH grant GM044783 and the Materials Research Science and Engineering Center at the University of Wisconsin-Madison (NSF DMR-0520527). The Magnetic Resonance Facility was supported by NSF grant CHE-9208463 and NIH grant RR08389. NMRFAM was supported by NIH grant P41RR02301. Read 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 Graphical Abstract Watching C 'n' N: Hydrazones and oximes are common conjugates but are labile to hydrolysis. The hydrolytic stabilities of isostructural hydrazones and one oxime were determined at pD 5.0–9.0. The rate constant for the acid-catalyzed hydrolysis of the oxime was nearly 103-fold lower than those for simple hydrazones, and a trialkylhydrazonium ion (formed after condensation) was even more stable than the oxime. Supporting Information Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z802651_s.pdf or from the author. 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. References 1 1aJ. B. Conant, P. D. Bartlett, J. Am. Chem. Soc. 1932, 54, 2881–2899; 1bF. H. Westheimer, J. Am. Chem. Soc. 1934, 56, 1962–1965; 1cE. G. R. Ardagh, F. C. Rutherford, J. Am. Chem. Soc. 1935, 57, 1085–1088. 2 2aD. E. Metzler, M. Ikawa, E. Snell, J. Am. Chem. Soc. 1954, 76, 648–652; 2bD. E. Metzler, J. Am. Chem. Soc. 1957, 79, 485–490. 3 3aW. P. Jencks, J. Am. Chem. Soc. 1959, 81, 475–481; 3bB. M. Anderson, W. P. Jencks, J. Am. Chem. Soc. 1960, 82, 1773–1777; 3cR. Wolfenden, W. P. Jencks, J. Am. Chem. Soc. 1961, 83, 2763–2768; 3dE. H. Cordes, W. P. Jencks, J. Am. Chem. Soc. 1962, 84, 826–831; 3eE. H. Cordes, W. P. Jencks, J. Am. Chem. Soc. 1962, 84, 832–837; 3fE. H. Cordes, W. P. Jencks, J. Am. Chem. Soc. 1962, 84, 4319–4328; 3gE. G. Sander, W. P. Jencks, J. Am. Chem. Soc. 1968, 90, 6154–6162; 3hJ. M. Sayer, M. Peskin, W. P. Jencks, J. Am. Chem. Soc. 1973, 95, 4277–4287. 4E. H. Cordes, W. P. Jencks, J. Am. Chem. Soc. 1963, 85, 2843–2848. 5W. P. Jencks, Prog. Phys. Org. Chem. 1964, 2, 63–128. 6For a recent example, see: F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, Vol. A, 5th ed., Springer, New York, 2008, pp. 650–651. 7K. B. Wiberg, R. Glaser, J. Am. Chem. Soc. 1992, 114, 841–850. 8R. J. Johnson, J. Stieglitz, J. Am. Chem. Soc. 1934, 56, 1904–1908. 9For representative examples, see: 9aK. Rose, J. Am. Chem. Soc. 1994, 116, 30–33; 9bL. E. Canne, A. R. Ferre-D'Amare, S. K. Burley, S. B. H. Kent, J. Am. Chem. Soc. 1995, 117, 2998–3007; 9cK. Rose, W. Zeng, P.-O. Ragamey, I. V. Chernushevich, K. G. Standing, H. F. Gaertner, Bioconjugate Chem. 1996, 7, 552–556; 9dL. K. Mahal, K. J. Yarema, C. R. Bertozzi, Science 1997, 276, 1125–1128; 9eL. A. Marcaurelle, Y. S. Shin, S. Goon, C. R. Bertozzi, Org. Lett. 2001, 3, 3691–3694; 9fS. Raddatz, J. Mueller-Ibeler, J. Kluge, L. Wäß, G. Burdinski, J. R. Havens, T. J. Onofrey, D. Wang, M. Schweitzer, Nucleic Acids Res. 2002, 30, 4793–4802; 9gG. G. Kochendoerfer, S.-Y. Chen, F. Mao, S. Cressman, S. Traviglia, H. Shao, C. L. Hunter, D. W. Low, E. N. Cagle, M. Carnevali, V. Gueriguian, P. J. Keogh, H. Porter, S. M. Stratton, M. C. Wiedeke, J. Wilken, J. Tang, J. J. Levy, L. P. Miranda, M. M. Crnogorac, S. Kalbag, P. Botti, J. Schindler-Horvat, L. Savatski, J. W. Adamson, A. Kung, S. B. H. Kent, J. A. Bradburne, Science 2003, 299, 884–887; 9hI. Chen, M. Howarth, W. Lin, A. Y. Ting, Nat. Methods 2005, 2, 99–104; 9iA. Dirksen, T. M. Hackeng, P. E. Dawson, Angew. Chem. 2006, 118, 7743–7746; Angew. Chem. Int. Ed. 2006, 45, 7581–7584; 9jX. F. Guo, A. Whalley, J. E. Klare, L. M. Huang, S. O'Brien, M. Steigerwald, Nano Lett. 2007, 7, 1119–1122; 9kE. M. Kolonko, L. L. Kiessling, J. Am. Chem. Soc. 2008, 130, 5626–5627; 9lS. Park, M. N. Yousaf, Langmuir 2008, 24, 6201–6207. 10A. Dirksen, S. Dirksen, T. M. Hackeng, P. E. Dawson, J. Am. Chem. Soc. 2006, 128, 15602–15603. 11 11aP. A. S. Smith, E. E. Most, J. Org. Chem. 1957, 22, 358–362; 11bR. F. Smith, L. E. Walker, J. Org. Chem. 1962, 27, 4372–4375; 11cJ. S. Moore, S. I. Stupp, J. Org. Chem. 1990, 55, 3374–3377. 12C. H. DePuy, B. W. Ponder, J. Am. Chem. Soc. 1959, 81, 4629–4631. 13V. V. Zverev, T. N. Pyalaeva, L. V. Ermolaeva, N. A. Filippova, Y. P. Kitaev, Bull. Acad. Sci. USSR Div. Chem. Sci. (Engl. Transl.) 1977, 26, 1865–1869. 14 14aR. A. More O'Ferrall, D. M. O'Brien, D. G. Murphy, Can. J. Chem. 2000, 78, 1594–1612; 14bR. A. More O'Ferrall, D. O'Brien, J. Phys. Org. Chem. 2004, 17, 631–640. 15E. Buncel, I.-H. Um, Tetrahedron 2004, 60, 7801–7825. 16L. Pauling, The Nature of the Chemical Bond, 1st ed., Cornell University Press, Ithaca, 1939, p. 60. Citing Literature Volume47, Issue39September 15, 2008Pages 7523-7526 ReferencesRelatedInformation