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
Download PDF
Synthesis 2015; 47(10): 1479-1487
DOI: 10.1055/s-0034-1380267
DOI: 10.1055/s-0034-1380267
paper
Convergent and Facile Synthesis of Hybrid Sulfonophosphonodipeptides
Authors
Further Information
Publication History
Received: 29 December 2014
Accepted after revision: 01 February 2015
Publication Date:
02 March 2015 (online)
Abstract
A convergent and facile method has been developed for the preparation of hybrid sulfonophosphonodipeptides composed of 2-aminoalkanesulfonic acid and 1-aminoalkylphosphonic acid residues. A series of hybrid sulfonophosphonodipeptides were synthesized in satisfactory yields via the Mannich-type reaction of 2-(Cbz-amino)alkanesulfonamides, aldehydes, and phosphorus trichloride, followed by sequential hydrolysis. The reaction mechanism was proposed and verified by NMR tracing experiments.
Key words
hybrid peptide - hydrolysis - Mannich reaction - phosphonopeptide - sulfonamide - sulfonopeptideSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380267.
Copies of 1H NMR, 13C NMR, and 31P NMR spectra of the products 3, and 31P NMR spectra of the mechanism tracing experiments are included.
- Supporting Information (PDF)
-
References
- 1 For a review, see: Kafarski P, Lejczak B. In Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity . Kukhar VP, Hudson HR. John Wiley; Chichester: 2000. Chap. 6, 173
- 2 For a review, see: Yiotakis A, Georgiadis D, Matziari M, Makaritis A, Dive V. Curr. Org. Chem. 2004; 8: 1135
- 3 Picha J, Budesinsky M, Fieddler P, Sanda M, Jiracek J. Amino Acids 2010; 39: 1265
- 4 Bartlett PA, Giangiordano MA. J. Org. Chem. 1996; 61: 3433
- 5 Tsukamoto T, Flanary JM, Rojas C, Slusher BS, Valiaeva N, Coward JK. Bioorg. Med. Chem. Lett. 2002; 12: 2189
- 6 Sampson NS, Bartlett PA. Biochemistry 1991; 30: 2255
- 7a Isomura S, Ashley JA, Wirsching P, Janda KD. Bioorg. Med. Chem. Lett. 2002; 12: 861
- 7b Wagner J, Lerner RA, Barbas III CF. Bioorg. Med. Chem. 1996; 4: 901
- 8 Meyer JH, Bartlett PA. J. Am. Chem. Soc. 1998; 120: 4600
- 9 Kafardki P, Lejczak B In Aminophosphonic and Aminophosphinic Acids: Chemistry and Biological Activity . Kukhar VP, Hudson HR. John Wiley; Chichester: 2000. Chap. 12, 407-442
- 10 Elliott RL, Marks N, Berg MJ, Portoghese PS. J. Med. Chem. 1985; 28: 1208
- 11 For a review, see: Xu JX. Chin. J. Org. Chem. 2003; 23: 1
- 12 Moree WJ, Van der Marel GA, Liskamp RM. J. Tetrahedron Lett. 1991; 32: 409
- 13 Carson KG, Schwender CF, Shroff HN, Cochran NA, Gallant DL, Briskin MJ. Bioorg. Med. Chem. Lett. 1997; 7: 711
- 14a Chen SJ, Lin CH, Kwon DS, Walsh CT, Coward JK. J. Med. Chem. 1997; 40: 3842
- 14b Galeotti N, Coste J, Bedos P, Jouin P. Tetrahedron Lett. 1996; 37: 3997
- 15 For a review, see: Xu JX, Yu L. Chin. J. Synth. Chem. 1999; 7: 153
- 16 Lowik DW. P. M, Liskamp RM. J. Eur. J. Org. Chem. 2000; 1219
- 17 Moree WJ, van der Marel GA, Liskamp RM. J. J. Org. Chem. 1995; 60: 5157
- 18 For recent reviews, see: Science of Synthesis: Multicomponent Reactions . Vols 1–2. Mueller TJ. J. Georg Thieme Verlag; Stuttgart: 2014
- 19 For a review, see: Xu JX. Sci. Sin.: Chim. 2013; 43: 995
- 20 Yuan CY, Wang GH. Synthesis 1990; 256
- 21a Dai Q, Chen RY. Synth. Commun. 1997; 27: 415
- 21b Dai Q, Chen RY. Synth. Commun. 1997; 27: 3341
- 21c Liu H, Xu JX. Amino Acids 2005; 29: 241
- 22a Dai Q, Chen RY, Zhang CX, Liu Z. Synthesis 1998; 405
- 22b Xu JX, Ma Y, Duan LF. Heteroat. Chem. 2000; 11: 417
- 23 Xu JX, Fu NY. Synth. Commun. 2000; 30: 4137
- 24a Xu JX, Wei M. Synth. Commun. 2001; 31: 1489
- 24b Xu JX, Fu NY. J. Chem. Soc., Perkin Trans. 1 2001; 1223
- 25a Fu NY, Zhang QH, Duan LF, Xu JX. J. Pept. Sci. 2006; 12: 303
- 25b Liu H, Cai SZ, Xu JX. J. Pept. Sci. 2006; 12: 337
- 26 Xu JX, Gao YH. Synthesis 2005; 738
- 27 Li BN, Cai SZ, Du DM, Xu JX. Org. Lett. 2007; 9: 2257
Reference Ris Wihthout Link
- 28 Meng FH, Xu JX. Amino Acids 2010; 39: 533
Reference Ris Wihthout Link
- 29 Meng FH, Xu JX. Tetrahedron 2013; 69: 4944
Reference Ris Wihthout Link
- 30 He FD, Meng FH, Song XQ, Hu WX, Xu JX. Org. Lett. 2009; 11: 3922
- 31 Meng FH, He FD, Song XQ, Zhang LL, Hu WX, Liu G, Xu JX. Amino Acids 2012; 43: 423
Reference Ris Wihthout Link
- 32a Meng FH, Chen N, Xu JX. Sci. China: Chem. 2012; 55: 2548
- 32b Yang ZH, Xu JX. Synthesis 2013; 45: 1675
- 33 Bartlett PA, McLaren KL. Phosphorus Sulfur Relat. Elem. 1987; 33: 1
- 34 31P NMR data have not been reported for intermediates in this manuscript. 31P NMR data of HP(O)Cl2 and HP(O)(OH)Cl were verified by adding different amounts of water to a solution of PCl3 in CDCl3. In addition, they matched with the reported data of HP(O)(OH)F (δ = 2.7 ppm). See: Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis . Verkade JG, Quin LD. VCH; Deerfield Beach (FL, USA): 1987: 33