Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2015; 47(03): 387-394
DOI: 10.1055/s-0034-1379487
DOI: 10.1055/s-0034-1379487
paper
Preparation of 4-Halobenzoate-Containing Phosphane-Based Building Blocks for Labeling Reactions Using the Traceless Staudinger Ligation
Further Information
Publication History
Received: 05 September 2014
Accepted after revision: 07 October 2014
Publication Date:
20 November 2014 (online)
Dedicated to the memory of Dr. Rainer Evers (Universität Rostock), deceased November 2013
Abstract
Functionalized phosphane-containing key building blocks were synthesized that are suitable for the labeling of biologically active molecules by the traceless Staudinger ligation. Thus, a 2-(diphenylphosphanyl)phenyl 4-stannylbenzoate building block was converted into the 4-iodobenzoate by the introduction of iodine. The traceless Staudinger ligation was used to introduce the resulting 4-iodobenzoate moiety into selected molecules of pharmacological interest. Furthermore, the labeling procedure was used to insert the 4-iodobenzoate moiety into a peptide on solid support. Finally, a convenient recovery procedure of the key phosphane building block 2-(diphenylphosphanyl)phenol from 2-(diphenylphosphoryl)phenol was evaluated.
Supporting Information
- Supporting information for this article, including 1H and 13C NMR spectra, for this article is available online at http://dx.doi.org/10.1055/s-0034-1379487.
- Supporting Information
-
References
- 1 Staudinger H, Meyer J. Helv. Chim. Acta 1919; 2: 635
- 2 Köhn M, Breinbauer R. Angew. Chem. Int. Ed. 2004; 43: 3106
- 3 van Berkel SS, van Eldijk MB, van Hest JC. M. Angew. Chem. Int. Ed. 2011; 50: 8806
- 4 Schilling CI, Jung N, Biskup M, Schepers U, Bräse S. Chem. Soc. Rev. 2011; 40: 4840
- 5 Nilsson BL, Kiessling LL, Raines RT. Org. Lett. 2000; 2: 1939
- 6 Saxon E, Armstrong JI, Bertozzi CR. Org. Lett. 2000; 2: 2141
- 7 Sletten EM, Bertozzi CR. Angew. Chem. Int. Ed. 2009; 48: 6974
- 8 Carroll L, Evans HL, Aboagye EO, Spivey AC. Org. Biomol. Chem. 2013; 11: 5772
- 9 King M, Wagner A. Bioconjugate Chem. 2014; 25: 825
- 10 Montalbetti CA. G. N, Falque V. Tetrahedron 2005; 61: 10827
- 11a Tsao M.-L, Tian F, Schultz PG. ChemBioChem 2005; 6: 2147
- 11b Wodtke R, König J, Pigorsch A, Köckerling M, Mamat C. Dyes Pigm. 2015; 113: 263
- 12 Pretze M, Wuest F, Peppel T, Köckerling M, Mamat C. Tetrahedron Lett. 2010; 51: 6410
- 13 Pretze M, Flemming A, Köckerling M, Mamat C. Z. Naturforsch. B. 2010; 65: 1128
- 14 Carroll L, Boldon S, Bejot R, Moore JE, Declerck J, Gouverneur V. Org. Biomol. Chem. 2011; 9: 136
- 15 Nilsson BL, Kiessling LL, Raines RT. Org. Lett. 2001; 3: 9
- 16 Kleineweischede R, Hackenberger CP. R. Angew. Chem. Int. Ed. 2008; 47: 5984
- 17 Soellner MB, Dickson KA, Nilsson BL, Raines RT. J. Am. Chem. Soc. 2003; 125: 11790
- 18 Grandjean C, Boutonnier A, Guerreiro C, Fournier J.-M, Mulard LA. J. Org. Chem. 2005; 70: 7123
- 19 Pötzsch R, Fleischmann S, Tock C, Komber H, Voit BI. Macromolecules 2011; 44: 3260
- 20 David O, Meester WJ. N, Bieräugel H, Schoemaker HE, Hiemstra H, van Maarseveen JH. Angew. Chem. Int. Ed. 2003; 42: 4373
- 21 Masson G, den HartogT, Schoemaker HE, Hiemstra H, van Maarseveen JH. Synlett 2006; 865
- 22 Bianchi A, Bernardi B. J. Org. Chem. 2006; 71: 4565
- 23 Nisic F, Speciale G, Bernardi A. Chem. Eur. J. 2012; 18: 6895
- 24 Bräse S, Gil C, Knepper K, Zimmermann V. Angew. Chem. Int. Ed. 2005; 44: 5188
- 25 Debets MF, van der Doelen CW. J, Rutjes FP. J. T, van Delft FL. ChemBioChem 2010; 11: 1168
- 26 Mamat C, Flemming A, Köckerling M, Steinbach J, Wuest FR. Synthesis 2009; 3311
- 27 Tam A, Soellner MB, Raines RT. J. Am. Chem. Soc. 2007; 129: 11421
- 28 Hermanson GT. Bioconjugate Techniques . Academic Press; London: 2008
- 29 Debets MF, van Hest JC. M, Rutjes FP. J. T. Org. Biomol. Chem. 2013; 11: 6439
- 30 Jamous M, Haberkorn U, Mier W. Molecules 2013; 18: 3379
- 31 Pretze M, Pietzsch D, Mamat C. Molecules 2013; 18: 8618
- 32 Zhou D, Zhou H, Jenks CC, Lewis JS, Katzenellenbogen JA, Welch MJ. Bioconjugate Chem. 2009; 20: 808
- 33 Lang L, Li W, Jia H.-M, Fang D.-C, Zhang S, Sun X, Zhu L, Ma Y, Shen B, Kiesewetter DO, Niu G, Chen X. Theranostics 2011; 1: 341
- 34 Mäding P, Füchtner F, Wüst F. Appl. Radiat. Isot. 2005; 63: 329
- 35 Kuchar M, Pretze M, Kniess T, Steinbach J, Pietzsch J, Löser R. Amino Acids 2012; 43: 1431
- 36 Vaidyanathan G, Zalutsky MR. Nature Protoc. 2006; 1: 707
- 37 Koziorowski J, Henssen C, Weinreich R. Appl. Radiat. Isot. 1998; 49: 955
- 38 Kapty J, Kniess T, Wuest F, Mercer JR. Appl. Radiat. Isot. 2011; 69: 1218
- 39 Talanov VS, Garmestani K, Regino CA. S, Milenic DE, Plascjak PS, Waldmann TA, Brechbiel MW. Nucl. Med. Biol. 2006; 33: 469
- 40 Mamat C, Franke M, Peppel T, Köckerling M, Steinbach J. Tetrahedron 2011; 67: 4521
- 41 Coenen HH, Mertens J, Mazière B. Radioiodination Reactions for Radiopharmaceuticals . Springer; Dordrecht: 2006: 29-44
- 42 Kometani T, Watt DS, Ji T. Tetrahedron Lett. 1985; 26: 204
- 43 Muhammad A. J. Chem. Soc. Pak. 1988; 10: 141
- 44 Bricklebank N, Godfrey SM, Mackie AG, McAuliffe CA, Pritchard RG, Kobryn PJ. J. Chem. Soc., Dalton Trans. 1993; 101
- 45 Hammerschmidt F, Simov BP, Schmidt S, Schneider S, Zolle I. Monatsh. Chem. 2005; 136: 229
- 46 Merkx R, Rijkers DT. S, Kemmink J, Liskamp RM. J. Tetrahedron Lett. 2003; 44: 4515
- 47 Soellner MB, Tam A, Raines RT. J. Org. Chem. 2006; 71: 9824
- 48 Liu L, Hong Z.-Y, Wong C.-H. ChemBioChem 2006; 7: 429
- 49 Mühlberg M, Jaradat DM. M, Kleineweischede R, Papp I, Dechtrirat D, Muth S, Broncel M, Hackenberger CP. R. Bioorg. Med. Chem. 2010; 18: 3679
- 50 Nilsson BL, Hondal RJ, Soellner MB, Raines RT. J. Am. Chem. Soc. 2003; 125: 5268
- 51 Chrencik JE, Brooun A, Recht MI, Nicola G, Davis LK, Abagyan R, Widmer H, Pasquale EB, Kuhn P. J. Biol. Chem. 2007; 282: 36505
- 52 Pretze M, Kuchar M, Bergmann R, Steinbach J, Pietzsch J, Mamat C. ChemMedChem 2013; 8: 935
- 53 Herd O, Heßler A, Hingst M, Tepper M, Stelzer O. J. Organomet. Chem. 1996; 522: 69
- 54 Horner L, Hoffmann H, Beck P. Chem. Ber. 1958; 91: 1583
- 55 Yanilkin VV, Gromakov YS, Nigmadzyanov FF. Russ. Chem. Bull. 1996; 45: 1257
- 56 Zhang T.-X, Zhang W.-X, Luo M.-M. Chin. Chem. Lett. 2014; 25: 176
- 57 Byrne PA, Rajendran KV, Muldon J, Gilheany DG. Org. Biomol. Chem. 2012; 10: 3531
- 58 Kenny NP, Rajendran KV, Jennings EV, Gilheany DG. Chem. Eur. J. 2013; 19: 14210
- 59 Sheldrick GM. SHELXS-97 and SHELXL-97, Programs for the Solution and Refinement of Crystal Structure. University of Göttingen; Germany: 1997
- 60 Sheldrick GM. Acta Crystallogr., Sect. A 2008; 64: 112