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Synthesis 2014; 46(01): 67-72
DOI: 10.1055/s-0033-1340089
DOI: 10.1055/s-0033-1340089
paper
Solution-Phase Synthesis of Chiral N-, O-, and S-Acyl Isopeptides
Further Information
Publication History
Received: 25 September 2013
Accepted after revision: 11 October 2013
Publication Date:
26 November 2013 (online)
Abstract
A convenient synthesis of chiral N-, O-, and S-acyl monoiso- and diisopeptides from di- and tripeptides containing tryptophan, tyrosine, and cysteine units using benzotriazole is reported in solution phase.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Tam JP, Lu Y.-A. J. Am. Chem. Soc. 1995; 117: 12058
- 2 Guichou J.-F, Patiny L, Mutter M. Tetrahedron Lett. 2002; 43: 4389
- 3 Alexander I, Raimo F, Antje R, Tatjana A, Lothar J. Eur. Pat. Appl EP 2487183 A1 20120815, 2012 ; Chem. Abstr. 2012, 157, 349369.
- 4a Yoshiya T, Taniguchi A, Sohma Y, Fukao F, Nakamura S, Abe N, Ito N, Skwarczynski M, Kimura T, Hayashi Y, Kiso Y. Org. Biomol. Chem. 2007; 5: 1720
- 4b Sohma Y, Taniguchi A, Skwarczynski M, Yoshiya T, Fukao F, Kimura T, Hayashi Y, Kiso Y. Tetrahedron Lett. 2006; 47: 3013
- 5 Popov V, Panda SS, Katritzky AR. Org. Biomol. Chem. 2013; 11: 1594
- 6 Popov V, Panda SS, Katritzky AR. J. Org. Chem. 2013; 78: 7455
- 7 Panda SS, El-Nachef C, Bajaj K, Youbi AO, Oliferenko AA, Katritzky AR. Chem. Biol. Drug. Des. 2012; 80: 821
- 8 Ha K, Chahar M, Monbaliu J.-CM, Todadze E, Hansen FK, Oliferenko AA, Ocampo CE, Leino D, Lillicotch A, Stevens CV, Katritzky AR. J. Org. Chem. 2012; 77: 2637
- 9 Katritzky AR, Tala SR, Dya NE. A, Ibrahim TS, E-Feky SA, Gyanda K, Pandya KM. J. Org. Chem. 2011; 76: 85
- 10 Coin I, Dolling R, Krause E, Bienert M, Beyermann M, Sferdean CD, Carpino LA. J. Org. Chem. 2006; 71: 6171
- 11 Taniguchi A, Yoshiya T, Abe N, Fukao F, Sohma Y, Kimura T, Hayashi Y, Kiso Y. J. Pept. Sci. 2007; 13: 868
- 12 Lecaillon J, Gilles P, Subra G, Martinez J, Amblard M. Tetrahedron Lett. 2008; 49: 4674
- 13 Yoshiya T, Kawashima H, Sohma Y, Kimura T, Kiso Y. Org. Biomol. Chem. 2009; 7: 2894
- 14 Tailhades J, Gidel M.-A, Grossi B, Lecaillon J, Brunel L, Subra G, Martinez J, Amblard M. Angew. Chem. Int. Ed. 2010; 49: 117
- 15 Taniguchi A, Sohma Y, Kimura M, Okada T, Ikeda K, Hayashi Y, Kimura T, Hirota S, Matsuzaki K, Kiso Y. J. Am. Chem. Soc. 2006; 128: 696
- 16 Taniguchi A, Sohma Y, Hirayama Y, Mukai H, Kimura T, Hayashi Y, Matsuzaki K, Kiso Y. ChemBioChem 2009; 10: 710
- 17 Mutter M, Chandravarkar A, Boyat C, Lopez J, Santos SD, Mandal B, Mimna R, Murat K, Patiny L, Saucede L, Tuchscherer G. Angew. Chem. Int. Ed. 2004; 43: 4172
- 18 Kiewitz SD, Kakizawa T, Kiso Y, Cabrele C. J. Pept. Sci. 2008; 14: 1209
- 19 Hentschel J, Krause E, Borner HG. J. Am. Chem. Soc. 2006; 128: 7722
- 20 Akira S, Daisuke T, Naomi N, Shugo T, Kohji I, Akira O. ChemBioChem 2007; 8: 1929
- 21 Perello MV, Hori Y, Ribo M, Muir TW. Angew. Chem. Int. Ed. 2008; 47: 7764
- 22 Boussert S, Perez ID, Kogan MJ, Oliveira E, Giralt E. ACS Nano 2009; 3: 3091
- 23 Bajaj K, Panda SS, Nachef CE, Katritzky AR. Chem. Biol. Drug Des. 2012; 80: 17
- 24 Panda SS, Bajaj K, Meyers MJ, Sverdrup FM, Katritzky AR. Org. Biomol. Chem. 2012; 10: 8985
- 25 Katritzky AR, Angrish P, Todadze E. Synlett 2009; 2392
- 26 Anderson GW. French patent FR 1406785 A, 1965 ; Chem. Abstr. 1965, 63, 72439.
- 27 Katritzky AR, Suzuki K, Singh SK. Synthesis 2004; 2645