Bisphosphine-functionalized cyclic decapeptides based on the natural product gramicidin s: A potential scaffold for transition-metal coordination

Chemistry - A European Journal

Volumn 15, Issue 33, 2009, Pages 8134-8145

  Burck, Sebastian ^a   Van Assema, Sander G A ^a   Lastdrager, Bas ^b   Slootweg, J Chris ^a   Ehlers, Andreas W ^a   Otero, José M ^c   Dacunha Marinho, Bruno ^c   Llamas Saiz, Antonio L ^c   Overhand, Mark ^b   Van Raaij, Mark J ^c,d   Lammertsma, Koop ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

^b LEIDEN UNIVERSITY   (Netherlands)

^c UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^d INSTITUT DE BIOLOGIA MOLECULAR DE BARCELONA   (Spain)

Author keywords

Aniino acids; Pcplides; Phosphancs; Solid phase synthesis; X ray diffraction

Indexed keywords

ABSOLUTE STEREOCHEMISTRY; ALKYL CHAIN; AMINO ACID BUILDING BLOCKS; ANIINO ACIDS; BISPHOSPHINE; CARBON ATOMS; CHELATING LIGANDS; CLOSE PROXIMITY; ENANTIOPURE; ENANTIOSELECTIVE ALKYLATION; FUNCTIONALIZED; GRAMICIDIN S; LINEAR SEQUENCE; METAL COORDINATION; NATURAL PRODUCTS; NI COMPLEXES; OLIGOPEPTIDES; PCPLIDES; PHOSPHANCS; SCHIFF-BASE; SINGLE CRYSTAL X-RAY STRUCTURES; SIZE AND SHAPE; SOLID-PHASE; SOLID-PHASE SYNTHESIS;

ALKYLATION; AMINATION; AMINES; AMINO ACIDS; CRYSTAL ATOMIC STRUCTURE; DIFFRACTION; FUNCTIONAL GROUPS; HYDROCARBONS; LIGANDS; ORGANIC ACIDS; PEPTIDES; PHOSPHORUS COMPOUNDS; SCAFFOLDS; STEREOCHEMISTRY; TRANSITION METALS; X RAY DIFFRACTION;

SYNTHESIS (CHEMICAL);

BIOLOGICAL PRODUCT; CYCLOPEPTIDE; GRAMICIDIN; LIGAND; PHOSPHINE; PHOSPHINE DERIVATIVE; TRANSITION ELEMENT;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; X RAY DIFFRACTION;

AMINO ACID SEQUENCE; BIOLOGICAL PRODUCTS; GRAMICIDIN; LIGANDS; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC; PHOSPHINES; TRANSITION ELEMENTS; X-RAY DIFFRACTION;

EID: 68949101686     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901127     Document Type: Article

References (88)

1. a) M. Limbach, Chem. Biodiversity 2005, 2, 825-836;
2. b) H. Wennemers, Chimia 2007, 61, 276-278;
3. c) R.V. Ulijn, A.M. Smith, Chem. Soc. Rev. 2008, 37, 664-675;
4. d) G. H. Gellman, Acc. Chem. Res. 1983, 16, 173-180;
5. e) D. Seebach, A. K. Beck, D.J. Bierbaum, Chem. Biodiversity 2004, 1, 1111-1239.
6. a) S. J. Miller, Acc. Chem. Res. 2004, 37, 601-610;
7. b) E. A. C. Davie, S. M. Mennen, Y. Xu, S. I Miller, Chem. Rev. 2007, 107, 5759-5812;
8. c) E. R. Jarvo, S. J. Miller, Tetrahedron 2002, 58, 2481-2495.
9. a) B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776-1779;
10. Angew. Chem. Int. Ed. Engl. 1996, 35, 1668-1671;
11. b) K. D. Shimizu, B. M. Cole, C. A. Krueger, K. W. Kuntz, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1997, 109, 1782-1785;
12. Angew. Chem. Int. Ed. Engl. 1997, 36, 1704-1707;
13. c) S. J. Degrado, H. Mizutani, A. H. Hov-eyda, J. Am. Chem. Soc. 2001, 123, 755-756;
14. d) C. A. LuchacoCullis, H. Mizutani, K. E. Murphy, A. H. Hoveyda, Angew. Chem. 2001, 113, 1504-1508;
15. Angew. Chem. Int. Ed. 2001, 40, 1456-1460;
16. e) H. Mizutani, S. J. Degrado, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 779-780;
17. f) A. W. Hird, A. H. Hoveyda, Angew. Chem. 2003, 115, 1314-1317;
18. Angew. Chem. Int. Ed. 2003, 42, 1276-1279;
19. g) A. H. Hoveyda, A. W. Hird, M. A. Kacprzynski, Chem. Commun. 2004, 1779-1785;
20. h) M. K. Brown, S.J. Degrado, A. H. Hoveyda, Angew. Chem. 2005, 117, 5440-5444;
21. Angew. Chem. Int. Ed. 2005, 44, 5306-5310;
22. i) C. Gennari, U. Pinarulli, Chem. Rev. 2003, 103, 3071-3100.
23. a) S. R. Gilbertson, G. Chen, M. McLoughlin, J. Am. Chem. Soc. 1994, 116, 4481-4482;
24. b) S. R. Gilbertson, X. Wang, G. S. Hoge, C. A. Klug, J. Schaefer, Organometallics 1996, 15, 4678-4680;
25. c) S. R. Gilbertson, X. Wang, J. Org. Chem. 1996, 61, 434-435;
26. d) S. R. Gilbertson, G. W. Starkey, J. Org. Chem. 1996, 61, 2922-2939;
27. e) S. R. Gilbertson, R. V. Pawlick, Angew. Chem. 1996, 108, 963-966;
28. Angew. Chem. Int. Ed. Engl. 1996, 35, 902-904;
29. f) S. R. Gilbertson, G. Chen, J. Kao, A. Beatty, C. F. Campana, J. Org. Chem. 1997, 62, 5557-5566;
30. g) S. R. Gilbertson, X. Wang, Tetrahedron 1999, 55, 11609-11618;
31. h) S. R. Gilbertson, S. E. Collibee, A. Agarkov, J. Am. Chem. Soc. 2000, 122, 6522-6523;
32. i) A. Agarkov, E. W. Uffman, S. R. Gilbertson, Org. Lett. 2003, 5, 2091-2094;
33. j) S. J. Greenfield, A. Agarkov, S. R. Gilbertson, Org. Lett. 2003, 5, 3069-3072;
34. k) A. Agarkov, S.J. Greenfield, T. Ohishi, S. E. Collibee, S. R. Gilbertson, J. Org. Chem. 2004, 69, 8077-8085;
35. l) A. Agarkov, S. R. Gilbertson, Tetrahedron Lett. 2005, 46, 181-183;
36. m) A. Agarkov, S. Greenfield, D. Xie, R. Pawlick, G. Starkey, S. R. Gilbertson, Biopolymers 2006, 84, 48-73;
37. n) C. A. Christensen, M. Meldal, Chem. Eur. J. 2005, 11, 4121-4131;
38. o) S. R. Gilbertson, X. Wang, Tetrahedron Lett. 1996, 37, 6475-6478.
39. A. L. Llamas-Saiz, G. M. Grotenbreg, M. Overhand, M. J. van Raaij, Acta Crystallogr. Sect. D 2007, 63, 401-407.
40. G. N. Tishchenko, V. I. Andrianov, B. K. Vainstein, M. M. Woolfson, E. Dodson, Acta Crystallogr. Sect. D 1997, 53, 151-159.
41. J. Omelanczuk, M. Mikolajczyk, Tetrahedron Lett. 1984, 25, 2493-2496.
42. a) D. A. Evans, T. C. Britton, J. Am. Chem. Soc. 1987, 109, 6881-6883;
43. b) D. A. Evans, J. A. Ellman, J. Am. Chem. Soc. 1989, 111, 1063-1072;
44. c) D. A. Evans, T. C. Britton, J. A. Ellman, R. I. Dorow, J. Am. Chem. Soc. 1990, 112, 4011-4030.
45. P. Knochel, M. C. P. Yeh, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390-2392.
46. L.R Rozhko, V. V. Ragulin, E. N. Tsvetkov, Russ. J. Gen. Chem. 1997, 67, 1861-1863.
47. Yu. N. Belokon, A. G. Bulychev, S. V. Vitt, Yu. T. Struchkov, A. S. Batsanov, T. V. Timofeeva, V. A. Tsyryapkin, M. G. Ryzhov, L. A. Lysova, V. I. Bakhmutov, V. M. Belikov, J. Am. Chem. Soc. 1985, 107, 4252-4259.
48. a) V. A. Soloshonok, T. Yamada, H. Ueki, A. M. Moore, T. K. Cook, K. L. Arbogast, A. V. Soloshonok, C. H. Martin, Y. Ohfune, Tetrahedron 2006, 62, 6412-6419;
49. b) A. S. Saghiyan, S. A. Dadayan, S. G. Petrosyan, L. L. Manasyan, A. V. Geolchanyan, S. M. Djamgaryan, S. A. Andreasyan, V. I. Maleev, V. N. Khrustalev, Tetrahedron: Asymmetry 2006, 17, 455-467;
50. c) Yu. N. Belokon, V. I. Maleev, T. F. Savel'eva, M. A. Moskalenko, D. A. Pripadchev, V. N. Khrustalev, E. V. Vorontsov, A. S. Sagiyan, E. P. Babayan, Russ. Chem. Bull. 2005, 114, 981-987;
51. d) X. Gu, J. M. Ndungu, W. Qiu, J. Ying, M. D. Carducci, H. Wooden, V. J. Hruby, Tetrahedron 2004, 60, 8233-8243;
52. e) A. S. Saghiyan, A. V. Geolchanyan, S. G. Petrosyan, T. V. Ghochikyan, V. S. Haroutunyan, A. A. Avetisyan, Yu. N. Belokon, K. Fisher, Tetrahedron: Asymmetry 2004, 15, 705-711.
53. V. A. Soloshonok, Yu. N. Belokon, N. A. Kuzmina, V. I. Maleev, N. Yu. Svistunova, V. A. Solodenko, V. P. Kukhar, J. Chem. Soc. Perkin Trans. 1 1992, 1525-1529.
54. D. I. Lobanov, I. M. Aladzheva, O. V. Bykhovskaya, P. V. Petrovskii, K. A. Lysenko, M. Yu. Antipin, T. A. Mastryukova, M. I. Kabachnik, Phosphorus Sulfur Silicon Relat. Elem. 1997, 128, 165-177.
55. A. N. Popkov, M. Nadvornik, J. Jiman, Ya. Sopkova, P. A. Manorik, M. A. Fedorenko, Russ. J. Gen. Chem. 1998, 68, 1305-1308.
56. J. Heinicke, N. Paulecke, P. G. Jones, Chem. Commun. 2005, 262-264.
57. J. A. van Doom, N. Meijboom, J. Chem. Soc. Perkin Trans. 2 1989, 1309-1313.
58. a) J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543-2549;
59. b) J. M. Seco, E. Quiñoá, R. Riguera, Chem. Rev. 2004, 104, 17-118.
60. a) H. Klostermeyer, Chem. Ber. 1968, 101, 2823-2831;
61. b) G. Losse, K. Neubert, Tetrahedron Lett. 1970, 11, 1267-1270;
62. c) K. Sato, H. Abe, T. Kato, N. Izumiya, Bull. Chem. Soc. Jpn. 1977, 50, 1999;
63. d) S. Aimoto, Bull. Chem. Soc. Jpn. 1988, 61, 2220-2222;
64. e) D. S. Wishart, L. H. Kondejewski, P. D. Semchuk, B. D. Sykes, R. S. Hodges, Lett. Pep. Sci. 1996, 3, 53-60;
65. f) M. Xu, N. Nishino, H. Mihara, T. Fujimoto, N. Izumiya, Chem. Lett. 1992, 191-194;
66. g) D. Andreu, S. Ruiz, C. Carreño, J. Alsina, F. Albericio, M. A. Jiménez, N. de La Figuera, R. Herranz, M. T. Garcia-López, R. González-Muniz, J. Am. Chem. Soc. 1997, 119, 10579-10586;
67. h) T. Arai, N. Maruo, Y. Sumida, C. Korousue, N. Nishino, Chem. Commun. 1999, 1503-1504;
68. i) X. Bu, X. Wu, G. Xie, Z. Guo, Org. Lett. 2002, 4, 2893-2895;
69. j) C. Qin, X. Bu, X. Wu, Z. Guo, J. Comb. Chem. 2003, 5, 353-355;
70. k) X. Wu, X. Bu, K. M. Wong, W. Yan, Z. Guo, Org. Lett. 2003, 5, 1749-1752;
71. l) G. M. Grotenbreg, M. Kronemeijer, M. S. M. Timmer, F. El Oualid, R. M. van Well, M. Verdoes, E. Spalburg, P. A. V. van Hooft, A. J. de Neeling, D. Noort, J. H. van Boom, G A. van der Marel, H. S. Overkleeft, M. Overhand, J. Org. Chem. 2004, 69, 7851-7859;
72. m) X. Bu, X. Wu, N. L. J. Ng, C. K. Mak, C. Qin, Z. Guo, J. Org. Chem. 2004, 69, 2681-2685;
73. n) P. Wadhwani, S. Afonin, M. Ieromino, A. S. Ulrich, J. Org. Chem. 2006, 71, 55-61.
74. a) G. M. Grotenbreg, A. E. M. Buizert, A. L. Llamas-Saiz, E. Spalburg, P. A. V. van Hooft, A. J. de Neeling, D. Noort, M. J. van Raaij, G. A. van der Marel, H. S. Overkleeft, M. Overhand, J. Am. Chem. Soc. 2006, 128, 7559-7565;
75. b) G M. Grotenbreg, M. S. M. Timmer, A. L. Llamas-Saiz, M. Verdoes, G A. van der Marel, M. J. van Raaij, H. S. Overkleeft, M. Overhand, J. Am. Chem. Soc. 2004, 126, 3444-3446.
76. S. Burck, H. Jansen, J. C. Slootweg, A. W. Ehlers, K. Lammertsma, unpublished results.
77. Y. N. Belokon, V. I. Tararov, V. I. Maleev, T. F. Savel'eva, M. G. Ryzhov, Tetrahedron: Asymmetry 1998, 9, 4249-4252.
78. a) N Braussaud, T. Ruether, K.J. Cavell, B. W. Skelton, A. H. White, Synthesis 2001, 0626-0632;
79. b) E. Kaiser, R. L. Colescot, C. D. Bossinge, P. I. Cook, Anal. Biochem. 1970, 34, 595-598;
80. c) C. Kay, O. E. Lorthioir, N. J. Parr, M. Congreve, S. C. McKeown, J. J. Scicinski, S. V. Ley, Biotechnol. Bioeng. 2000, 71, 110-118.
81. APEX2 Version 2009.1-0, Bruker AXS, Madison, 2009.
82. COLLECT, Nonius BV, R. W. Hooft, Delft, 1998.
83. Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307-326.
84. SADABS, G. M. Sheldrick, Bruker AXS, Madison, 1997.
85. L. Buts, M.-H. Dao-Thi, L. Wyns, R. Loris, Acta Crystallogr. Sect. D 2004, 60, 983-984.
86. M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Crystallogr. 2005, 38, 381-388.
87. G. M. Sheldrick, Acta Crystallogr. Sect. A 2008, 64, 112-122.
88. L. J. Farrugia, J. Appl. Crystallogr. 1999, 32, 837-838.