RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2014; 46(17): 2293-2296
DOI: 10.1055/s-0034-1378207
DOI: 10.1055/s-0034-1378207
special topic
Copper-Free Cleavage-Sonogashira Conjugation of Silylacetylene Immobilized Peptides
Weitere Informationen
Publikationsverlauf
Received: 28. Februar 2014
Accepted after revision: 05. Mai 2014
Publikationsdatum:
24. Juni 2014 (online)
Abstract
A one-pot copper-free fluoride-initiated method for the Sonogashira cross-coupling of SAM2-immobilized peptides is described.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
-
References
- 1a Massif C, Dautrey S, Haefele A, Ziessel R, Renard P.-Y, Romieu A. Org. Biomol. Chem. 2012; 10: 4330
- 1b Gauthier MA, Klok H.-A. Chem. Commun. 2008; 2591
-
2a Chinchilla R, Nájera C. Chem. Soc. Rev. 2011; 40: 5084
- 2b Sonogashira K, Tohda Y, Hagihara N. Tetrahedron Lett. 1975; 16: 4467
- 3a Ten Brink HT, Rijkers DT. S, Liskamp RM. J. J. Org. Chem. 2006; 71: 1817
-
3b Balraju V, Reddy DS, Periasamy M, Iqbal J. J. Org. Chem. 2005; 70: 9626
- 4a Hoffmanns U, Metzler-Nolte N. Bioconjugate Chem. 2006; 17: 204
- 4b Pfeiffer H, Rojas A, Niesel J, Schatzschneider U. Dalton Trans. 2009; 4292
- 4c Brosch O, Weyhermüller T, Metzler-Nolte N. Eur. J. Inorg. Chem. 2000; 323
- 4d Brosch O, Weyhermüller T, Metzler-Nolte N. Inorg. Chem. 1999; 38: 5308
- 5a Rijkers DT. S, Diederich F. Tetrahedron Lett. 2011; 52: 4021
- 5b Bong DT, Ghadiri MR. Org. Lett. 2001; 3: 2509
- 6a Strack M, Langklotz S, Bandow JE, Metzler-Nolte N, Albada HB. J. Org. Chem. 2012; 77: 9954
- 6b Strack M, Metzler-Nolte N, Albada HB. Org. Lett. 2013; 15: 3126
- 7 For example, the acronym ‘SAM’ is also used for S-adenosinyl methionine, for spin angular momentum, and for self-assembled monolayer.
- 8 This was shown in ref. 6a, where a separated cleavage and click method yielded the peptide in 16%, whereas a one-pot cleavage-click protocol resulted in 59% yield.
- 9a Liao Y, Fathi R, Reitman M, Zhang Y, Yang Z. Tetrahedron Lett. 2001; 42: 1815
- 9b Leikoski T, Kallonen S, Yli-Kauhaluoma J. Helv. Chim. Acta 2010; 93: 39
- 9c Utesch NF, Diederich F. Org. Biomol. Chem. 2003; 1: 237
- 9d Tan DS, Foley MA, Shair MD, Schreiber SL. J. Am. Chem. Soc. 1998; 120: 8565
- 9e Aucagne V, Berteina-Raboin S, Guenot P, Agrofoglio LA. J. Comb. Chem. 2004; 6: 717
- 9f Spivey AC, McKendrick J, Srikaran R, Helm BA. J. Org. Chem. 2003; 68: 1843
- 9g Utesch NF, Diederich F, Boudon F, Gisselbrecht J.-P, Gross M. Helv. Chim. Acta 2004; 87: 698
- 9h Liao Y, Fathi R, Yang Z. J. Comb. Chem. 2003; 5: 79
- 9i Cassel JA, Leue S, Gachkova NI, Kann NC. J. Org. Chem. 2002; 67: 9460
- 9j Brun V, Legraverend M, Grierson DS. Tetrahedron 2002; 58: 7911
- 9k Brun V, Legraverend M, Grierson DS. Tetrahedron Lett. 2001; 42: 8169
- 9l Charton J, Cousaert N, Bochu C, Willand N, Déprez B, Déprez-Poulain R. Tetrahedron Lett. 2007; 48: 1479
- 9m Meloni MM, White PD, Armour D, Brown RC. D. Tetrahedron 2007; 63: 299
- 9n Elliott EL, Ray CR, Kraft S, Atkins JR, Moore JS. J. Org. Chem. 2006; 71: 5282
- 9o Yao T, Yue D, Larock RC. J. Comb. Chem. 2005; 7: 809
- 9p Hwang J.-J, Tour JM. Tetrahedron 2002; 58: 10387
- 10 The strategy somewhat resembles the resin-to-resin transfer reaction: Tulla-Puche J, Barany G. Tetrahedron 2005; 61: 2195
- 11a Hatanaka Y, Matsui K, Hiyama T. Tetrahedron Lett. 1989; 30: 2403
- 11b Zhou Z.-L, Zhao L, Zhang S, Vincent K, Lam S, Henze D. Synth. Commun. 2012; 42: 1622
- 12a Wang L, Pinhua L. Synth. Commun. 2003; 33: 3679
- 12b Drescher S, Becker S, Dobner B, Blume A. RSC Adv. 2012; 2: 4052
- 12c Suzuki N, Yasaki S, Yasuhara A, Sakamoto T. Chem. Pharm. Bull. 2003; 51: 1170
- 13 Astruc D, Boisselier E, Ornelas C. Chem. Rev. 2010; 110: 1857