The synthesis of a glucoconjugate of the peptidic fragment of cryptophycin-24

Authors

  • Abdelmoumen Mezrai Laboratory of Organic Chemistry, Natural Products and Analyse. University of Tlemcen. P.O Box 119. 13 000 Tlemcen, Algeria
  • David Lesur Laboratoire des Glucides. FRE CNRS 3517. Université de Picardie Jules Verne, 33 rue Saint-Leu, F-80039 Amiens Cedex, France.
  • Anne Wadouachi Laboratoire des Glucides. FRE CNRS 3517. Université de Picardie Jules Verne, 33 rue Saint-Leu, F-80039 Amiens Cedex, France.
  • Florence Pilard Laboratoire des Glucides. FRE CNRS 3517. Université de Picardie Jules Verne, 33 rue Saint-Leu, F-80039 Amiens Cedex, France.
  • Joseph Kajima Mulengi Laboratory of Organic Chemistry, Natural Products and Analyse. University of Tlemcen. P.O Box 119. 13 000 Tlemcen, Algeria

DOI:

https://doi.org/10.13171/mjc.3.4.2014.04.07.15

Abstract

A novel glucoconjugate of the peptidic fragment of cryptophycin-24 was prepared through the replacement of the leucic acid residue with L-leucine and the functionalisation of tyrosine residue with glucose.Those modifications lead to a novel protected tripeptide fragment of cryptophycin-24.

References

- G. Trimurtulu, I. Ohtani, G.M.L. Patterson, R. E. Moore, T. H. Corbett, F. A. Valeriote, and L. Demchiko, J. Am. Chem. Soc. 1994, 116, 4729-4737.

- R. E. Moore, T. H. Corbett, G. M. L. Patterson, and F. A. Valeriote, Curr. Pharm. Des. 1996, 2, 317- 330.

- S. Chaganty, G. Trimurtulu, C. E. Heltzel, R. E. Moore, and W. Y. Yoshida, J. Nat. Prod. 2004, 67, 1403-1406.

- G. V. Subbaraju, G. Trimurtulu, G. M. L. Patterson, and R. E. Moore, J. Nat. Prod. 1997, 60, 302-305.

- (a) J. D. White, Jian Hong, and L. A. Robarge, J. Org. Chem. 1999, 64, 6206-6216.

(b) Ghosh, A. K.; Swanson, L. J. Org. Chem. 2003, 68, 9823-9826.

- B. H. Norman, T. Hemscheidt, R. M. Schultz, and S. I. Andis, J. Org. Chem. 1998, 63, 5288-5294.

- J. Liang, E. D. Moher, R. E. Moore, and D. W. Hoard, J. Org. Chem. 2000, 65, 3143-3147.

- A. K. Ghosh, and A. Bischoff, Org. Lett., 2000, 2 (11), 1573-1575.

- U. P. Dhokte, V. V. Khau, D. R. Hutchison, and M. J. Martinelli, Tetrahedron Lett. 1998, 39, 8771-8774.

- N. K. Tripathy, and G. I. Georg, G. I. Tetrahedron Lett. 2004, 45, 5309–5311.

- M. Kobayashi, W. Wang, N. Ohyabu, M. Kurosu,.and I. Kitagawa, Chem. Pharm. Bull. 1995, 43, 1598-1600.

- J. D. White, J. Hong, J.; Robarge, L. A. J. Org. Chem. 1999, 64, 6206-6216.

- M. Eggen, C. J. Mossman, S. B. Buck, S. K. Nair, L. Bhat, S. M. Ali, E. A. Reiff, T. C. Boge, and G. I. Georg, J. Org. Chem. 2000, 65, 7792-7799.

- MJ. Eggen, S. K. Nair, and G. I. Georg, Org. Lett. 2001, 3, 1813-1815.

- M. A. Tius, Tetrahedron 2002, 58, 4343-4367.

- R. E. Schwartz, C. F. Hirsch, D. F. Sesin, J. E. Flor, M. Chartrain, R. E. Fromtling, G. H. Harris, M. J. Salvatore, J. M. Liesch, and K. Yudin, J. Ind. Microbiol. 1990, 5, 113-124.

- N. A. Magarvey, Z. Q. Beck, G. Trimurtulu, Y. Ding, U. Huber, T. K. Hemscheidt, D. Abelson, R. E. Moore, and D. H. Sherman, ACS Chem. Biol., 2006, 1 (12), 766-779

- S. Eissler, M. Nahrwold, B. Neumann, H-G. Stammler, and Sewald, N. Org. Lett.2007, 9 (5), 817-819.

- M. Nahrwold, T. Bogner, S. Eissler, S. Verma, and N. Sewald, Org. Lett.2010, 12 (5), 1064-1067.

- M. J. Eggen, and G. I. Georg, Bioorg. Med. Chem. Lett. 1998, 8, 3177-3180.

- a) R. Vidya, MJ. Eggen, G. I. Georga, and R. H. Himes, Bioorg. Med. Chem. Lett. 2003, 13, 757–760.

b) C. Weiï¢, T. Bogner, B. Sammett and N. Sewald Beilstein J. Org. Chem. 2012, 8, 2060-2066.

- S. B. Buck, J.K. Huff, R. H. Himes, and G. I. Georg, J. Med. Chem. 2004, 47, 696- 702.

- C. Shih, L. S. Gossett, J. M. Gruber, C. S. Grossman, S. L. Andis, R. M.; J. F. Schultz, Worzalla, T. H. Corbett, and J. T. Metz, Bioorg. Med. Chem. Lett. 1999, 9, 69-74.

- R. Vidya, MJ. Eggen, S. K. Nair, G. I. Georg, and R. H. Himes, J. Org. Chem. 2003, 68, 9687-9693.

- R. S. Al-awar, J. E. Ray, R. M. Schultz, S. L. Andis, J. H. Kennedy, R. E. Moore, L. Liang, G. Trimurtulu, G. V. Subbaraju, and T. H. Corbett, J. Med. Chem. 2003, 46, 2985-3007.

- M. Furuyama, and I. Shimizu, Tetrahedron: Asymmetry 1998, 9, 1351-1357.

- M. Lautens, and M. L. Maddess, Org. Lett., 2004, 6 (12), 1883-1886.

- A. B. Smith, Y. Shin Cho, G. R. Pettit, and R. Hirschmann, Tetrahedron 2003, 59, 6991-7009.

- C. Pousset, M. Haddad, and M. Larchevêque, Tetrahedron, 2001, 57, 7163-7167.

- A. B. Smith, Y. Shin Cho, L. E. Zawacki, R. Hirschmann,, and G. R. Pettit, Org. Lett., 2001, 3 (25), 4063-4066.

– V. F. Patel, S. L. Andis, J. H. Kennedy, J. E. Ray, and R. M. Schultz, J. Med. Chem. 1999, 42, 2588-2603.

- S. Raghavan, and K. A. Tony, J. Org. Chem. 2003, 68, 5002-5005.

- W. L. Liu, J. C. Zhang, F. Qin Jiang, and L. Fu, Arch. Pharm. Chem. Life Sci. 2009, 342, 577-583.

- J. M. de Muys, R. Rej, D. Nguyen, B. Go, S. Fortin, and J-F. Lavallée, Bioorg.Med. Chem. Lett., 1996, 6, 1111-1116.

- R. Rej, D. Nguyen, B. Go, S. Fortin, and J-F. Lavallée, J. Org. Chem. 1996, 61, 6289-6295.

- J. Cooksey, A. Gunn, P. J. Kocienski, A. Kuhl, S. Uppal, J. A. Christopher, and R. Bell, Org. Biomol. Chem., 2004, 2, 1719-1731.

- J. A. McCubbin, M. L. Maddess, and M. Lautens, Org. Lett., 2006, 8(14), 2993-2996.

- C. A. Mast, S. E. A. Stoncˇius, H-G. Stammler, B. Neumann, and N. Sewald, Chem. Eur. J. 2005, 11, 4667-4677.

- S. Eißler, T. Bogner, M. Nahrwold, and N. Sewald, Chem. Eur. J. 2009, 15, 11273-11287.

- R. A. Barrow, T. Hemscheidt, J. Liang, S. Paik, R. E. Moore, and M.A. Tius, J. Am. Chem. Soc. 1995, 117, 2479-2490.

- K. M. Gardinier, and J. W. Leahy, J. Org. Chem. 1997, 62, 7098-7099.

- J. Liang, R. E. Moore, E. D. Moher, J. E. Munroe, R. S. Al-awar, D. A. Hay, D. L. Varie, T. Y. Zhang, J. A. Aikins, M. J. Martinelli, C. Shih, J. E. Ray, L. L. Gibson, V. Vasu Vasudevan, L. Polin, K. White, J. Kushner, C. Simpson, S. Pugh, and T. H. Corbett, Investig. New Drugs 2005, 23, 213-224.

- S. M. Ali, and G. I. Georg, Tetrahedron Lett., 1997, 38, 1703-1706.

- G. I. Georg, S. M. Ali, V. J. Stella, W. N. Waugh, and R. H. Himes, Bioorg. Med. Chem. Lett. 1998, 8, 1959-1962.

- (a) S. B. Buck, J. K. Huff, R. H. Himes, and G. I. Georg, J. Med. Chem. 2004, 47, 696-702.

(b) S. B. Buck, J. K. Huff, R. H. Himes, and G. I. Georg, J. Med. Chem. 2004, 47, 3697-3699.

- G. M. Salamonczyk, Kang Han, Zhi-wei Guo, and Charles J. Sih J. Org. Chem. 1996, 61, 6893-6900.

- F. Z.Baba Ahmed, H. Merzouk, S. Bouanane, N. B. Benkalfat, S. A. Merzouk, J. Kajima Mulengi,and M. Narcel, Ann. Toxicol. Anal. 2010, DOI : 10. 1051/ata/2010017.

- S. Koide, and S. Sidhu ACS. Chem. Biol. 2009, 4, 325-334.

- (a) C. Dye, and B. G. Williams, Science, 2010, 328, 856-861.

(b) B. Cao, and S. Williams, J. Nat. Prod. Rep. 2010, 27, 919-947.

(c) K. Ohtsubo, and J. D. Marth, Cell 2006, 126, 855-867.

(d) S. M. Muthana, C. T. Campbell, and J. C. Gildersleeve, ACS Chem. Biol. 2012, 7, 31-43.

(e) Xi Chen ACS Chem. Biol. 2011, 6(1), 14-17.

(f) B. Cao, J. M. White, and S. J. Williams, Beilstein J. Org. Chem. 2011, 7, 369-377.

- (a) J. A. Singh, Chun-Xiao Xu, Xiaoming Xu, L. M. West, A. Wilines, A. Chan, E. Hamel, J. H. Miller, P. T. Northcote, and A. K. Ghosh, J. Org. Chem. 2010, 75, 2-10.

(b) J. G. Swoboda, E. Mylonakis, B. J. Wilkinson, and S. Walker, ACS Chem. Biol. 2011, 6, 106-116).

(c) T. J. Boltje, T. Buskas, and G. J. Boons, Nature Chemistry, 2009, 1, 611-622.

- G. J. L. Bermudes, B. Castagner, and P. H. Seeberg, ACS Chem Biol. 2009, 4, 703-713.

- L. Schofield, M. C. Hewitt, K. Evans, M. A. Siomos, and P. H. Seeberg, Nature, 2002, 418, 785-789.

- (a) J. A. Prescher, and C. R. Bertozzi, Cell 2006, 126, 851-854.

(b) O. T. Keppler, R. Horstkorte, M. Pawlita, C. Schmidt, and W. Reutter, Glycobiology 2001, 11, 11R-18R.

- (a) I. O. Potapenko, V. D. Haaneken, T. Luders, A. Helland, I. Bukholm, T. Sorlie, V. N. Kristensen, O. C. Lingjaerde, and A. L. Borresen-Dale, Mol. Oncol. 2010, 4, 98-118.

(b) H. Yu, and X. Chen, Org. Biomol. Chem. 2007, 5, 865-872.

(c) M. Gutterigg, S. Burgmayr, G. Poltl, J. Rudolf, and E. Staudacher, Glycoconjugates J. 2007, 24, 475-489.

- C. I. Gama, S. E. Tully, N. Sotogatu, P. M. Clark, M. Rawat, N. Vaidehi, W. A. Goddard, 3rd, A. Nishi, and L. C. Hsieh-Wilson, Nat. Chem. Biol. 2006, 2, 467-473.

- B. S. Furniss, A. J. Hannaford, V. Rogers, P. W. G. Smith A. R. Tatchell, Vogel’s Textbook of Practical Organic Chemistry, 4th Edition, Longman Group Limited, London, 1978, ISBN 0-582-44250-8, p454-455.

- a) B. S. Furniss, A. J. Hannaford, V. Rogers, P. W. G. Smith A. R. Tatchell, Vogel’s Textbook of Practical Organic Chemistry, 4th Edition, Longman Group Limited, London, 1978, ISBN 0-582-44250-8, p457-458)

b) S. Pearson, W. Scarano, M. H. Stenzel Chem. Commun. 2012.

- N. Imai, T. Kometani , P. J. Crocker, J. B. Bowdan, A. Demir, L. D. Dwyer, D. M. Mann, T. C. Vanaman, and D. S. Watt, Bioconjugate Chem. 1990, 1(2), 138-143.

- J. G. Herandez, and E. Juaristi, J. Org. Chem. 2010, 75, 7107-7111

Downloads

Published

2014-07-04

Issue

Section

Organic Chemistry