Metathesis reactions of carbohydrates: Recent highlights in cross-metathesis

European Journal of Organic Chemistry

Volumn , Issue 32, 2010, Pages 6123-6143

  Aljarilla, Ana ^a   López, J Cristóbal ^b   Plumet, Joaquín ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Carbohydrates; Cross metathesis; Cyclodextrins; Glycoconjugates; Porphyrins

Indexed keywords

EID: 78249240865     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000570     Document Type: Review

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198. Trisaccharide 103 was synthesized from trisaccharide 172 by CM reaction with trans-2-butene in the presence of catalyst 2. On the other hand, trisaccharide 172 was prepared by glycosylation of 170 (J. R. Allen, J. G. Allen, X.-F. Zhang, L. J. Williams, A. Zatorski, G. Ragupathi, P. O. Livingston, S. J. Danishefsky, Chem. Eur. J. 2000, 6, 1366-1375) with glycosyl fluoride 170 (K. C. Nicolaou, T. Caulfield, H. Kataoka, T. Kumazawa, J. Am. Chem. Soc. 1988, 110, 7910-7912).
199. CM reaction of 172 and amino acid 12 also works in the presence of catalyst 5. See:, J. Zhu, Q. Wan, G. Yang, O. Ouerfelli, S. J. Danishefsky, Heterocycles 2009, 79, 441 - 449.
200. FMOC Solid Phase Peptide Synthesis. A Practical Approach (Eds.:, W. C. Chan, P. D. White), Oxford University Press, New York, 2000.
201. G. B. Fields, R. L. Noble, Int. J. Pept. Protein Res. 1990, 35, 161 - 286.
202. C. G. Fields, D. H. Lloyd, R. L. McDonald, K. M. Otteson, R. L. Noble, Pept. Res. 1991, 4, 95 - 101.
203. L. A. Marcaurelle, C. R. Bertozzi, Glycobiology 2002, 12, 69 - 77.
204. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride. This carbodiimide reagent and its urea by-product are water soluble. Thus, the byproduct and any excess reagent are removed by aqueous extraction.
205. 1-Hydroxybenzotriazol is a reagent normally used as a racemization suppressor, and to improve yields in peptide synthesis.
206. In this case, Fmoc deprotection was achieved by using diethylamine instead of piperidine for reasons of volatility.
207. For selected references, see
208. W. Koenig, R. Geiger, Chem. Ber. 1970, 103, 2034 - 2040.
209. L. A. Carpino, A. El-Faham, F. Albericio, J. Org. Chem. 1995, 60, 3561 - 3564.
210. T. Kawakami, S. Yoshimura, S. Aimoto, Tetrahedron Lett. 1998, 39, 7901 - 7904.
211. [70]
212. Conjugate 116 was prepared for biological evaluation.
213. This reagent provides an effective means for linking synthetic peptide antigens to MAP (Multiple Antigenic Peptides) or carrier proteins for the purpose of raising antibodies.
214. Some dimers were obtained by disulfide formation. Recuperation of the monomeric compounds was carried out by reduction with tris(2-carboxyethyl) phosphane (TCEP).
215. m-Maleimidobenzoyl-N-hydroxysuccinimide (MBS) and its water-soluble analog sulfo-MBS, are heterobifunctional cross-linkers that contain N-hydroxysuccinimide (NHS) ester and maleimide groups that allow covalent conjugation of amine- and sulfhydryl-containing molecules.
216. The Porphyrin Handbook, vol. 10 (Eds.:, K. Kadish, K. M. Smith, R. Guilard), Academic Press, San Diego, 1999.
217. B. D. Berezin, in: Coordination Compounds of Porphyrins and Phthalocyanins, John Wiley, Chichester, 1981.
218. For selected reviews, see
219. S. Wang, R. Gao, F. Zhou, M. Selke, J. Mater. Chem. 2004, 14, 487 - 493.
220. L. M. Moreira, F. V. dos Santos, J. P. Lyon, M. Maftoum-Costa, C. Pacheco-Soares, N. S. da Silva, Aust. J. Chem. 2008, 61, 741 - 754.
221. T. Dai, Y.-Y. Huang, M. R. Hamblin, Photodiagn. Photodyn.Ther. 2009, 6, 170 - 188.
222. C. A. Robertson, D. H. Evans, H. Abrahamse, J. Photochem. Photobiol. B: Biology 2009, 96, 1 - 8.
223. For a survey on the toxicity of photoactivated artificial porphyrins through porphyrin-protein interaction, see:, A. Smith, Anal. N.Y. Acad. Sci. 1987, 514, 309 - 322.
224. Selected reviews
225. E. L. Clennan, Tetrahedron 2000, 56, 9151 - 9179.
226. M. C. de Rosa, R. J. Crutchley, Coord. Chem. Rev. 2002, 233, 351 - 371.
227. J. Baier, T. Fuss, C. Pöllmann, C. Wiesmann, K. Pindl, R. Engl, D. Baumer, M. Maier, M. Landthaler, W. Bäumler, J. Photochem. Photobiol. B: Biology 2007, 87, 163 - 173.
228. M. Cornia, C. Valenti, S. Capacchi, P. Cozzini, Tetrahedron 1998, 54, 8091 - 8106.
229. For a review on the synthesis of glycoporphyrins, see:, J. A. S. Cavaleiro, J. P. C. Tomé, M. A. F. Faustino, in: Topics in Heterocyclic Chemistry (Ed.:, E. S. H. El Ashry), Springer, Berlin, 2007, vol. 7, pp. 179-248.
230. However, other metathetical processes have been used for the synthesis of porphyrin glycoconjugates. See, for instance
231. G. Zheng, A. Graham, M. Shibata, J. R. Missert, A. R. Oseroff, T. J. Dougherty, R. K. Pandey, J. Org. Chem. 2001, 66, 8709-8716 (enyne metathesis). On the other hand, functionalized porphyrins have been constructed by means of metathesis reactions. See, for instance
232. C. Ikeda, A. Satake, Y. Kobuke, Org. Lett. 2003, 5, 4935-4938 (macrocyclization of porphyrins by RCM)
233. P. C. M. van Gerven, J. A. A. W. Elemans, J. W. Gerritsen, S. Speller, R. J. M. Nolte, A. E. Rowan, Chem. Commun. 2005, 3535-3537 (porphyrin "boxes" by CM-RCM sequence)
234. S. J. Langford, M. J. Latter, C. P. Woodward, Org. Lett. 2006, 8, 2595-2598 (multiporphyrin arrays by selective CM)
235. L. Jiao, E. Hao, F. R. Fronczek, M. G. H. Vicente, K. M. Smith, Chem. Commun. 2006, 3900-3902 (benzoporphyrins by RCM).
236. F. C. da Silva, V. F. Ferreira, M. C. B. V. de Souza, A. C. Tomé, M. G. P. M. S. Neves, A. M. S. Silva, J. A. S. Cavaleiro, Synlett 2008, 1205 - 1207.
237. J. Szejtli, Pure Appl. Chem. 2004, 76, 1825 - 1845.
238. E. M. Martín del Valle, Process Biochem. 2004, 39, 1033 - 1046.
239. Cyclodextrin and Their Complexes (Ed.:, H. Dodziuk), Wiley-VCH, Weinheim, 2006.
240. K. Uekama, F. Hirayama, T. Irie, Chem. Rev. 1998, 98, 2045 - 2076.
241. Metathesis reactions other than CM have been used for the synthesis of functionalized cyclodextrins. See, for instance
242. O. Bistri, T. Lecourt, J.-M. Mallet, M. Sollogoub, P. Sinaÿ, Chem. Biodiversity 2004, 1, 129-137 (Sonogashira coupling followed by RCM)
243. T. Lecourt, J.-M. Mallet, P. Sinaÿ, C. R. Chim. 2003, 6, 87-90 (RCM)
244. T. Lecourt, J.-M. Mallet, P. Sinaÿ, Eur. J. Org. Chem. 2003, 4553-4560 [acyclic diene metathesis (ADMET) followed by RCM]
245. T. Lecourt, J.-M. Mallet, P. Sinaÿ, Tetrahedron Lett. 2002, 43, 5533 - 5536.
246. According to Liu and Chen, ". bridged bis(β-cyclodextrins) can enhance the original binding ability and molecular selectivity of native β-cyclodextrin and thus be successfully utilized in drug carriers, solubilizers, catalysis, photochemical materials, etc."; see
247. Y. Liu, Y. Chen, Acc. Chem. Res. 2006, 39, 681 - 691. For selected references in this context, see
248. R. Breslow, B. Zhang, J. Am. Chem. Soc. 1996, 118, 8495-8496 (cholesterol recognition and binding by cyclodextrin dimers)
249. A. Ruebner, J. G. Moser, D. Kirsch, B. Spengler, S. Andrees, S. Rohers, J. Incl. Phenom. Macrocycl. Chem. 1996, 25, 35-38 (cyclodextrin dimers as carriers for photodynamic therapy of cancer). For other selected reviews, see
250. F. van de Manakker, T. Vermonden, C. F. van Nostrum, W. E. Hennink, Biomacromolecules 2009, 10, 3157 - 3175.
251. [104], footnote 9.
252. S.-H. Chiu, D. C. Myles, R. L. Garrell, J. F. Stoddart, J. Am. Chem. Soc. 2000, 65, 2792 - 2796.
253. For a report concerning the synthesis of bis(β-cyclodextrin) derivatives as carriers for gadolinium complexes using analogous methodology, see:, S. Aime, E. Gianolio, G. Palmisano, B. Robaldo, A. Barge, L. Boffa, G. Cravotto, Org. Biomol. Chem. 2006, 4, 1124 - 1130.
254. S.-H. Chiu, D. C. Myles, J. Org. Chem. 1999, 64, 332 - 333.
255. B. B. Ghera, F. Fache, H. Parrot-López, Tetrahedron 2006, 62, 4807 - 4813. In this report also a dimer of compound 156 was synthesized using catalyst 2.