A synthetic method for diversification of the P1′ substituent in phosphinic dipeptides as a tool for exploration of the specificity of the S1′ binding pockets of leucine aminopeptidases

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 9, 2007, Pages 3187-3200

  Vassiliou, Stamatia ^a   Xeilari, Metaxia ^a   Yiotakis, Athanasios ^a   Grembecka, Jolanta ^b   Pawełczak, Małgorzata ^c   Kafarski, Paweł ^b,c   Mucha, Artur ^b  

^a UNIVERSITY OF ATHENS   (Greece)

^b WROCLAW UNIVERSITY OF TECHNOLOGY   (Poland)

^c UNIVERSITY OF OPOLE   (Poland)

Author keywords

Alkylation; Cross coupling; LAP inhibitors; P1 diversification; Phosphinic pseudodipeptides

Indexed keywords

ALKYL GROUP; AMINO ACID; AMINOPEPTIDASE; CYTOSOL AMINOPEPTIDASE; DIPEPTIDE DERIVATIVE; ENZYME INHIBITOR; HYDROGEN; MICROSOMAL AMINOPEPTIDASE; PHENYLALANINE DERIVATIVE; PROTEINASE;

ARTICLE; COMPUTER AIDED DESIGN; CYTOSOL; DERIVATIZATION; ENZYME ACTIVITY; ENZYME SPECIFICITY; HYDROGEN BOND; PEPTIDE SYNTHESIS; PREDICTION;

BINDING SITES; DIPEPTIDES; HYDROGEN BONDING; LEUCYL AMINOPEPTIDASE; LIGANDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHINIC ACIDS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33947602399     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.02.042     Document Type: Article

References (54)

1. Taylor A. Trends Biochem. Sci. 18 (1993) 167-171
2. Taylor A. FASEB J. 7 (1993) 290-298
3. Current Topics: Aminopeptidases in Health and Disease. Biol. Pharm. Bull. 2004, 27, 760-780.
4. Sträter N., and Lipscomb W.N. In: Barrett A.J., Rawlings N.D., and Woessner J.F. (Eds). Handbook of Proteolytic Enzymes (2002), Academic Press, Amsterdam 1384-1389
5. Lowther W.T., and Matthews B.W. Chem. Rev. 102 (2002) 4581-4607
6. Burley S.K., David P.R., Taylor A., and Lipscomb W.N. Proc. Natl. Acad. Sci. U.S.A. 87 (1990) 6878-6882
7. Burley S.K., David P.R., Sweet R.M., Taylor A., and Lipscomb W.N. J. Mol. Biol. 224 (1992) 113-140
8. Kim H., Burley S.K., and Lipscomb W.N. J. Mol. Biol. 230 (1993) 722-724
9. Kim H., and Lipscomb W.N. Biochemistry 32 (1993) 8465-8478
10. Sträter N., and Lipscomb W.N. Biochemistry 34 (1995) 9200-9210
11. Kim H., and Lipscomb W.N. Adv. Enzymol. Relat. Areas Mol. Biol. 68 (1994) 153-213
12. Sträter N., and Lipscomb W.N. Biochemistry 34 (1995) 14792-14800
13. Sträter N., Sun L., Kantrowitz E.R., and Lipscomb W.N. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 11151-11155
14. Schürer G., Horn A.H.C., Gedeck P., and Clark T. J. Phys. Chem. B 106 (2002) 8815-8830
15. Erhardt S., Jaime E., and Weston J. J. Am. Chem. Soc. 127 (2005) 3654-3655
16. York I.A., Goldberg A.L., Mo X.Y., and Rock K.L. Immunol. Rev. 172 (1999) 49-66
17. Jösch C., Klotz L.-O., and Sies H. Biol. Chem. 384 (2003) 213-218
18. Cappiello M., Lazzarotti A., Buono F., Scaloni A., D'Ambrosio C., Amodeo P., Méndez B.L., Pelosi P., Del Corso A., and Mura U. Biochem. J. 378 (2004) 35-44
19. Pulido-Cejudo G., Conway B., Proulx P., Brown R., and Izaguirre C.A. Antiviral Res. 36 (1997) 167-177
20. Beninga J., Rock K.L., and Goldberg A.L. J. Biol. Chem. 273 (1998) 18734-18742
21. Taylor A., Daims M., Lee J., and Surgenor T. Curr. Eye Res. 2 (1982) 47-56
22. Umezawa H. Recent Results Cancer Res. 75 (1980) 115-125
23. Gupta S.K., Aziz M., and Khan A.A. Indian J. Pathol. Microbiol. 32 (1989) 301-305
24. Grembecka J., and Kafarski P. Mini-Rev. Med. Chem. 1 (2001) 133-144
25. Giannousis P.P., and Bartlett P.A. J. Med. Chem. 30 (1987) 1603-1609
26. Lejczak B., Kafarski P., and Zygmunt J. Biochemistry 28 (1989) 3549-3555
27. Grembecka J., Mucha A., Cierpicki T., and Kafarski P. J. Med. Chem. 46 (2003) 2641-2655
28. Dra{ogonek}g M., Grembecka J., Pawelczak M., and Kafarski P. Eur. J. Med. Chem. 40 (2005) 764-771
29. Turner A.J. In: Barrett A.J., Rawlings N.D., and Woessner J.F. (Eds). Handbook of Proteolytic Enzymes (2002), Academic Press, Amsterdam 996-1000
30. Chen H., Roques B.P., and Fournié-Zaluski M.-C. Bioorg. Med. Chem. Lett. 9 (1999) 1511-1516
31. Bauvois B., and Dauzonne D. Med. Res. Rev. 26 (2006) 88-130
32. Insight 2000 Molecular Modelling Program Package; Accelrys, 2000.
33. Yiotakis A., Georgiadis D., Matziari M., Makaritis A., and Dive V. Curr. Org. Chem. 8 (2004) 1135-1158
34. Georgiadis D., Matziari M., Vassiliou S., Dive V., and Yiotakis A. Tetrahedron 55 (1999) 14635-14648
35. Photaki I. J. Am. Chem. Soc. 85 (1963) 1123-1126
36. Yiotakis A., Vassiliou S., Jiráček J., and Dive V. J. Org. Chem. 61 (1996) 6601-6605
37. Ullmann F. Ber. Dtsch. Chem. Ges. 36 (1903) 2382-2384
38. for review, see. Lindley J. Tetrahedron 40 (1984) 1433-1456
39. Hartwig J.F. Angew. Chem., Int. Ed. 37 (1998) 2046-2067
40. Ma D., Zhang Y., Yao J., Wu S., and Tao F. J. Am. Chem. Soc. 120 (1998) 12459-12467
41. Kwong F.Y., Klapars A., and Buchwald S.L. Org. Lett. 4 (2002) 581-584
42. Wolfe J.P., and Buchwald S.L. J. Org. Chem. 65 (2000) 1144-1157
43. Salvatore R.N., Yoon C.H., and Jung K.W. Tetrahedron 57 (2001) 7785-7811
44. Salvatore R.N., Nagle A.S., and Jung K.W. J. Org. Chem. 67 (2002) 674-683
45. Gavin J.A., Garcia M.E., Benesi A.J., and Mallouk T.E. J. Org. Chem. 63 (1998) 7663-7669
46. Gall A.L., Ruff M., Kannan R., Cuniasse P., Yiotakis A., Dive V., Rio M.-C., Basset P., and Moras D. J. Mol. Biol. 307 (2001) 577-686
47. Grams F., Dive V., Yiotakis A., Yiallouros I., Vassiliou S., Zwilling R., Bode W., and Stöcker W. Nat. Struct. Biol. 3 (1996) 671-675
48. Selkti M., Tomas A., Gaucher J.-F., Prangé T., Fournié-Zaluski M.-C., Chen H., and Roques B.-P. Acta Cryst. D 59 (2003) 1200-1205
49. Kafarski L., and Lejczak B. In: Kukhar V.P., and Hudson H.R. (Eds). Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity (2000), John Wiley, Chichester 173-203 407-442
50. Collinsová M., and Jiráček J. Curr. Med. Chem. 7 (2000) 629-647
51. Dive V., Lucet-Levannier K., Georgiadis D., Cotton J., Vassiliou S., Cuniasse P., and Yiotakis A. Biochem. Soc. Trans. 28 (2000) 455-460
52. Dive V., Georgiadis D., Matziari M., Makaritis A., Beau F., Cuniasse P., and Yiotakis A. Cell. Mol. Life Sci. 61 (2004) 2010-2019
53. Cuniasse P., Devel L., Makaritis A., Beau F., Georgiadis D., Matziari M., Yiotakis A., and Dive V. Bichemie 87 (2005) 393-402
54. Discover, Molecular Modelling Program Package; Molecular Simulation 1997.