A straightforward synthetic access to symmetrical glycosyl disulfides and biological evaluation thereof(116 visite) Adinolfi M, Capasso D, Di Gaetano S, Iadonisi A, Leone L, Pastore A
*** IBB - CNR *** Dipartimento di Chimica Organica e Biochimica, Università Federico II di Napoli, via Cinthia 4, I-80126 Naples, Italy Facoltà di Scienze Biotecnologiche, Università di Napoli Federico II, via Mezzocannone 16, 80134 Naples, Italy Istituto di Biostrutture e Bioimmagini, CNR, via Mezzocannone 16, 80134 Naples, Italy Facolt di Scienze Biotecnologiche, Universit di Napoli Federico II, via Mezzocannone 16, 80134 Naples, Italy
Aversa, M.C., Barattucci, A., Bonaccorsi, P., (2009) Eur. J. Org. Chem., p. 6455
Stellenboom, N., Hunter, R., Caira, M.R., Szilagy, L., (2010) Tetrahedron Lett., 51, p. 5309
Valerio, S., Iadonisi, A., Adinolfi, M., Ravidà, A., (2007) J. Org. Chem., 72, p. 6097
Adinolfi, M., Iadonisi, A., Ravidà, A., Schiattarella, M., (2003) Tetrahedron Lett., 44, p. 7863
Ibatullin, F.M., Selivanov, S.I., Shavva, A.G., (2001) Synthesis, p. 419
Pezzella, A., Iadonisi, A., Valerio, S., Panzella, L., Napolitano, A., Adinolfi, M., D'Ischia, M., (2009) J. Am. Chem. Soc., 131, p. 15270. , For a stepwise approach to (phenylselenyl)thioglycosides and their application to protein glycoconjugation via disulfide linkage
Gamblin, D.P., Garnier, P., Van Kasteren, S., Oldham, N.J., Fairbanks, A.J., Davis, B.G., (2004) Angew. Chem., Int. Ed., 43, p. 828. , For a recent kinetic study on the formation of disulfide and SSe linkages
Steinmann, D., Nauser, T., Koppenol, W.H., (2010) J. Org. Chem., 75, p. 6696
Sharpless, K.B., Young, M.W., (1975) J. Org. Chem., 40, p. 947
Smith Iii, A.B., Richmond, R.E., (1983) J. Am. Chem. Soc., 105, p. 575
Martins Alho, M.A., D'Accorso, N.B., Thiel, I.M.E., (1996) J. Heterocycl. Chem., 33, p. 1339
Renaudie, L., Daniellou, R., Augè, C., Le Narvor, C., (2004) Carbohydr. Res., 339, p. 693
Gillies, R.G., Didier, N., Denton, M., (1986) Anal. Biochem., 159, p. 109
Andr, S., Pei, Z., Siebert, H. -C., Ramstr m, O., Gabius, H. -J., (2006) Bioorg. Med. Chem., 14, p. 6314
Richtmyer, N. K., Carr, C. J., Hudson, C. S., (1943) J. Am. Chem. Soc., 65, p. 1477
Kiefel, M. J., Thomson, R. J., Radovanovic, M., Von Itzstein, M., (1999) J. Carbohydr. Chem., 18, p. 937
Davis, B. G., Ward, S. J., Rendle, P. M., (2001) Chem. Commun., p. 189
Aversa, M. C., Barattucci, A., Bonaccorsi, P., (2009) Eur. J. Org. Chem., p. 6455
Ibatullin, F. M., Selivanov, S. I., Shavva, A. G., (2001) Synthesis, p. 419
Gamblin, D. P., Garnier, P., Van Kasteren, S., Oldham, N. J., Fairbanks, A. J., Davis, B. G., (2004) Angew. Chem., Int. Ed., 43, p. 828. , For a recent kinetic study on the formation of disulfide and SSe linkages
Sharpless, K. B., Young, M. W., (1975) J. Org. Chem., 40, p. 947
Smith Iii, A. B., Richmond, R. E., (1983) J. Am. Chem. Soc., 105, p. 575
Rajanbabu, T. V., Ayers, T. A., Halliday, G. A., You, K. K., Calabrese, J. C., (1997) J. Org. Chem., 62, p. 6012
Martins Alho, M. A., D'Accorso, N. B., Thiel, I. M. E., (1996) J. Heterocycl. Chem., 33, p. 1339
Gillies, R. G., Didier, N., Denton, M., (1986) Anal. Biochem., 159, p. 109
Symmetrical glycosyl disulfides can be prepared within a few hours from per-O-acetylated precursors via a sequential approach entailing short reactions and no purification of any intermediate. The final thiolate-to-disulfide oxidation step is noticeably accelerated by low amounts of phenyl diselenide under air. Applicability of the strategy to non-saccharidic symmetrical alkyl disulfides has also been examined. A preliminary assay of the cytotoxic activity of symmetrical 1,1'-disulfides was performed on two human tumor cell lines, and a noteworthy activity was recorded for a range of these synthetic compounds.
88 Records (82 escludendo Abstract e Conferenze). Impact factor totale: 347.772 (327.32 escludendo Abstract e Conferenze). Impact factor a 5 anni totale: 360.309 (336.443 escludendo Abstract e Conferenze).
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