Monatshefte für Chemie - Chemical Monthly

, Volume 142, Issue 12, pp 1289–1308 | Cite as

Synthesis and binding properties of guanidinium biscarboxylates

Original Paper

Abstract

The ammonium ion binding site of the enzyme glutaminase HisF inspired us to design guanidinium biscarboxylates as potential self-organized ionophores in molecular recognition. The syntheses of the title compounds based on aliphatic and aromatic building blocks, along with a general method for the preparation of δ-aminoethoxyacetic acids, are presented in this work. Investigation of the binding properties of the title compounds in dimethyl sulfoxide (DMSO) and methanol solution revealed no ammonium ion affinity, but interaction of the guanidinium moiety with acetate ions.

Graphical abstract

Keywords

Guanidinium Unnatural amino acid Recognition Ligand Pyrrole 

Notes

Acknowledgments

We thank the Deutsche Forschungsgemeinschaft (GRK 640) and the University of Regensburg for support of this work. We thank Dr. R. Vasold and K. Lehner for HPLC analyses.

Supplementary material

706_2011_660_MOESM1_ESM.docx (725 kb)
Supplementary material 1 (DOCX 725 kb)

References

  1. 1.
    Evans DA, Murry JA, von Matt P, Norcross RD, Miller SJ (1995) Angew Chem Int Ed 34:798Google Scholar
  2. 2.
    Evans DA, Johnson JS (1997) J Org Chem 62:786Google Scholar
  3. 3.
    Hechavarría Fonseca M, König B (2003) Adv Syn Cat 345:1173Google Scholar
  4. 4.
    Evans DA, Kozlowski MC, Burgey CS, MacMillan DWC (1997) J Am Chem Soc 119:7893Google Scholar
  5. 5.
    Sohtome Y, Hashimoto Y, Nagasawa K (2005) Adv Synth Catal 347:1643Google Scholar
  6. 6.
    Davis M, Bonnat M, Guillier F, Kilburn JD, Bradley M (1998) J Org Chem 63:8696Google Scholar
  7. 7.
    Hunter CA, Purvis DH (1992) Angew Chem Int Ed 31:792Google Scholar
  8. 8.
    Ragusa A, Rossi S, Hayes JM, Steinand M, Kilburn JD (2005) Chem Eur J 5:5674Google Scholar
  9. 9.
    Rensing S, Schrader T (2002) Org Lett 4:2161Google Scholar
  10. 10.
    Chang S-Y, Kim HS, Chang K-J, Jeong K-S (2004) Org Lett 6:181Google Scholar
  11. 11.
    Kovbasyuk L, Krämer R (2004) Chem Rev 104:3161Google Scholar
  12. 12.
    Chin J, Walsdorff C, Stranix B, Oh J, Chung HJ, Park SM, Kim K (1999) Angew Chem Int Ed 38:2756Google Scholar
  13. 13.
    Bell TW, Hext NM (2004) Chem Soc Rev 33:589Google Scholar
  14. 14.
    Raker J, Glass TE (2002) J Org Chem 67:6113Google Scholar
  15. 15.
    Holý P, Morf WE, Seller K, Simon W, Vigneron J-P (2004) Helv Chim Acta 73:1171Google Scholar
  16. 16.
    Krause C, Werner T, Huber C, Wolfbeis OS (1999) Anal Chem 71:1544Google Scholar
  17. 17.
    Shih Y, Huang HJ (1999) Anal Chim Acta 392:143Google Scholar
  18. 18.
    Lee MH, Yoo CL, Lee JS, Cho I-S, Kim BH, Cha GS, Nam H (2002) Anal Chem 74:2603Google Scholar
  19. 19.
    Riggs JA, Litchfield RK, Smith BD (1996) J Org Chem 61:1148Google Scholar
  20. 20.
    Tsukube H, Shinoda S, Uenishi J, Kanatani T, Itoh H, Shiode M, Iwachido T, Yonemitsu O (1998) Inorg Chem 37:1585Google Scholar
  21. 21.
    Boudouche S, Jacquet L, Lobo-Recio MA, Marzin C, Tarrago G (1993) J Inclusion Phenom Macrocyclic Chem 16:81Google Scholar
  22. 22.
    Metzger A, Gloe K, Stephan H, Schmidtchen FP (1996) J Org Chem 61:2051Google Scholar
  23. 23.
    Fricke T, Hamann J, Bahadir M, König B (2002) Anal Bioanal Chem 374:148Google Scholar
  24. 24.
    Stefan R-I, Baiulescu GE, Aboul-enien HY (1997) Crit Rev Analyt Chem 27:307Google Scholar
  25. 25.
    Fry CH, Hall SK, Blatter LA, McGuigan JAS (1990) Exp Physiol 75:187Google Scholar
  26. 26.
    Smith JW, Le Calvez H, Parra-Gessert L, Preece NE, Jia X, Assa-Munt N (2002) J Biol Chem 277:10298Google Scholar
  27. 27.
    Singh AK, Singh R, Saxena P (2004) Sensors 4:187Google Scholar
  28. 28.
    Peczuh MW, Hamilton AD (2000) Chem Rev 100:2479Google Scholar
  29. 29.
    Abbastabar-Ahangar H, Shirzadmehr A, Marjani K, Khoshsafar H, Chaloosi M, Mohammadi L (2009) J Inclusion Phenom Macrocyclic Chem 63:287Google Scholar
  30. 30.
    Mazurov A, Hauser T, Miller CH (2006) Curr Med Chem 13:1567Google Scholar
  31. 31.
    Alexandratos SD, Zhu X (2007) Inorg Chem 46:2139Google Scholar
  32. 32.
    Bülhman P, Prestch E, Bakker E (1998) Chem Rev 98:1593Google Scholar
  33. 33.
    Ehala S, Kasicka V, Makrlík E (2008) Electrophoresis 29:652Google Scholar
  34. 34.
    Bakker E (2004) Anal Chem 76:3285Google Scholar
  35. 35.
    Bakker E, Qin Y (2006) Anal Chem 78:3965Google Scholar
  36. 36.
    Jiang P, Guo Z (2004) Coord Chem Rev 248:205Google Scholar
  37. 37.
    Valeur B, Leray I (2000) Coord Chem Rev 202:40Google Scholar
  38. 38.
    de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Radermacher JT, Rice TE (1997) Chem Rev 97:1515Google Scholar
  39. 39.
    Spichiger UE, Freiner D, Bakker E, Rosatzin T, Simon W (1993) Sens Actuators B 11:263Google Scholar
  40. 40.
    Lübbers DW (1995) Acta Anaesthesiol Scand 39:37Google Scholar
  41. 41.
    Buck SM, Lee Koo Y-E, Park E, Xu H, Philbert MA, Brasuel MA, Kopelman R (2004) Curr Opin Chem Biol 8:540Google Scholar
  42. 42.
    Davidsohn I, Henry JB (1978) Clinical diagnosis by laboratory methods. WB Saunders, PhiladelphiaGoogle Scholar
  43. 43.
    Spichiger-Keller UE (1999) Analyt Chim Acta 400:65Google Scholar
  44. 44.
    Lehn JM (1995) Supramolecular chemistry—concepts and perspectives. VCH, New YorkGoogle Scholar
  45. 45.
    Kirkovits GJ, Shriver JA, Gale PA, Sessler JL (2001) J Inclusion Phenom Macrocyclic Chem 41:69Google Scholar
  46. 46.
    Izatt RM, Pawlak K, Bradshaw JS (1995) Chem Rev 95:2529Google Scholar
  47. 47.
    Zhang XX, Bradshaw JS, Izatt RM (1997) Chem Rev 97:3313Google Scholar
  48. 48.
    Grady T, Harris SJ, Smyth MR, Diamond D, Hailey P (1996) Anal Chem 68:3775Google Scholar
  49. 49.
    Grady T, Joyce T, Smyth MR, Harris SJ, Diamond D (1998) Anal Commun 35:123Google Scholar
  50. 50.
    Sakaki T, Harada T, Deng G, Kawabata H, Kawahara Y, Shinkai S (1992) J Inclusion Phenom Macrocyclic Chem 14:285Google Scholar
  51. 51.
    Kim H-J, Asif R, Chunga DS, Hong J-I (2003) Tetrahedron Lett 44:4335Google Scholar
  52. 52.
    Imai H, Misawa K, Munakata H, Uemori Y (2001) Chem Lett 688Google Scholar
  53. 53.
    Wright AT, Anslyn EV (2004) Org Lett 6:1341Google Scholar
  54. 54.
    Ahn KH, Kim S-G, Jung J, Kim K-H, Kim J, Chin J, Kim K (2000) Chem Lett 170Google Scholar
  55. 55.
    Tomas S, Prohens R, Vega M, Rotger MC, Deya PM, Ballester P, Costa A (1996) J Org Chem 61:9394Google Scholar
  56. 56.
    Jon SY, Kim J, Kim M, Park S-H, Jeon WS, Heo J, Kim K (2001) Angew Chem Int Ed 40:2116Google Scholar
  57. 57.
    Chin J, Walsdorff C, Stranix B, Oh J, Chung HJ, Park S-M, Kim K (1999) Angew Chem Int Ed 38:2756Google Scholar
  58. 58.
    Schmidtchen FP, Berger M (1997) Chem Rev 97:1609Google Scholar
  59. 59.
    Schrader T (1996) Angew Chem Int Ed 35:2649Google Scholar
  60. 60.
    Schrader T (1998) J Org Chem 63:264Google Scholar
  61. 61.
    Bell TW, Khasanov AB, Drew MGB (2002) J Am Chem Soc 124:14092Google Scholar
  62. 62.
    Bell TW, Hext NM, Khasanov AB (1998) Pure Appl Chem 70:2371Google Scholar
  63. 63.
    Rebek J Jr, Nemeth D (1985) J Am Chem Soc 107:6738Google Scholar
  64. 64.
    Fokkens M, Schrader T, Klärner F-G (2005) J Am Chem Soc 127:14415Google Scholar
  65. 65.
    Talbiersky P, Bastkowski F, Klärner FG, Schrader T (2008) J Am Chem Soc 130:9824Google Scholar
  66. 66.
    Aıt-Haddou H, Wiskur SL, Lynch VM, Anslyn EV (2001) J Am Chem Soc 123:11296Google Scholar
  67. 67.
    Zheng Y-S, Zhang C (2004) Org Lett 6:1189Google Scholar
  68. 68.
    Schmuck C, Bickert V (2007) J Org Chem 72:6832Google Scholar
  69. 69.
    Rehm T, Stepanenko V, Zhang X, Würthner F, Gröhn F, Klein K, Schmuck C (2008) Org Lett 10:1469Google Scholar
  70. 70.
    Calnan BJ, Tidor B, Biancalana S, Hudson D, Frankel AD (1991) Science 252:1167Google Scholar
  71. 71.
    Hancock RD, Melton DL, Harrington JM, McDonald FC, Gephart RT, Boone LL, Jones SB, Dean NE, Whitehead JR, Cockrell GM (2007) Coord Chem Rev 251:1678Google Scholar
  72. 72.
    Kruppa M, Mandl C, Miltschitzky S, König B (2005) J Am Chem Soc 127:3362Google Scholar
  73. 73.
    Escuder B, Rowan AE, Feiters MC, Nolte RJM (2004) Tetrahedron 60:291Google Scholar
  74. 74.
    Suzuki I, Obata K, Anzai J-I, Ikeda H, Ueno A (2000) J Chem Soc Perkin Trans II 1705Google Scholar
  75. 75.
    Gale PA (2003) Coord Chem Rev 240:191Google Scholar
  76. 76.
    Douangamath A, Walker M, Beismann-Driemeyer S, Vega-Fernandez MC, Sterner R, Wilmanns M (2002) Structure 10:185Google Scholar
  77. 77.
    Chandrakumar NS, Stapelfeld A, Beardsley PM, Lopez OT, Drury B, Anthony E, Savage MA, Williamson LN, Reichman M (1992) J Med Chem 35:2928Google Scholar
  78. 78.
    Korosec E, Poljsak D, Urleb U (1992) Arch Pharm 325:251Google Scholar
  79. 79.
    Garner P, Park JM (1998) Org Synth Coll 9:300Google Scholar
  80. 80.
    Meyers AI, McKennon MJ (1993) J Org Chem 58:3568Google Scholar
  81. 81.
    Depew KM, Marsden SP, Zatorska D, Zatorski A, Bornmann WG, Danishefsky SJ (1999) J Am Chem Soc 121:11953Google Scholar
  82. 82.
    Zhu Z, Espenson JH (1996) J Am Chem Soc 118:9901Google Scholar
  83. 83.
    Lottes AC, Landgrebe JA, Larsen K (1989) Tetrahedron Lett 30:4089Google Scholar
  84. 84.
    Fructos MR, Belderrain TR, de Frémont P, Scott NM, Nolan SP, Mar Díaz-Requejo M, Pérez PJ (2005) Angew Chem Int Ed 44:5284Google Scholar
  85. 85.
    Groziak MP, Townsend LB (1986) Org Chem 51:1277Google Scholar
  86. 86.
    Martin NI, Woodward JJ, Marletta MA (2006) Org Lett 8:4035Google Scholar
  87. 87.
    Martin NI, Beeson WT, Woodward JJ, Marletta MA (2008) J Med Chem 51:924Google Scholar
  88. 88.
    Lewellyn ME, Wang SS, Strydom PJ (1990) J Org Chem 55:5230Google Scholar
  89. 89.
    Suhs T, König B (2006) Chem Eur J 12:8150Google Scholar
  90. 90.
    Katritzky AR, Kirichenko N, Rogovoy BV, Kister J, Tao H (2004) Synthesis 1799 and literature thereinGoogle Scholar
  91. 91.
    Linton BR, Carr AJ, Orner BP, Hamilton AD (2000) J Org Chem 65:1566Google Scholar
  92. 92.
    Esmail R, Kurzer F (1975) Synthesis 301Google Scholar
  93. 93.
    Schmuck C, Lex J (1999) Org Lett 1:1779Google Scholar
  94. 94.
    SchmuckC (1999) Eur J Org Chem 2397Google Scholar
  95. 95.
    Schmuck C, Dudaczek J (2005) Tetrahedron Lett 46:7101Google Scholar
  96. 96.
    Schmuck C (2006) Coord Chem Rev 250:3053Google Scholar
  97. 97.
    Schmuck C, Bickert V (2003) Org Lett 5:4579Google Scholar
  98. 98.
    Schmuck C (2000) Chem Eur J 6:709Google Scholar
  99. 99.
    Schmuck C (1999) Chem Commun 843Google Scholar
  100. 100.
    Kyne GM, Light ME, Hursthouse MB, de Mendoza J, Kilburn JD (2001) J Chem Soc Perkin Trans I 1258Google Scholar
  101. 101.
    Hunter CA, Purvis DH (1992) Angew Chem Int Ed 31:792Google Scholar
  102. 102.
    Ragusa A, Rossi S, Hayes JM, Stein M, Kilburn JD (2005) Chem Eur J 5:5674Google Scholar
  103. 103.
    Chang S-Y, Kim HS, Chang K-J, Jeong K-S (2004) Org Lett 6:181Google Scholar
  104. 104.
    Schmuck C, Machon U (2005) Chem Eur J 11:1109Google Scholar
  105. 105.
    Fitzmaurice RJ, Gaggini F, Srinivasan N, Kilburn JD (2007) Org Biomol Chem 5:1706Google Scholar
  106. 106.
    Bourdais J, Omar A, Mohsen ME (1980) J Heterocycl Chem 17:555Google Scholar
  107. 107.
    Schwesinger R (1985) Chimica 39:269Google Scholar
  108. 108.
    Linton B, Hamilton AD (1999) Tetrahedron 55:6027 and literature thereinGoogle Scholar
  109. 109.
    Srinivasa Reddy D, Vander Velde D, Aube J (2004) J Org Chem 69:1716Google Scholar
  110. 110.
    Bonauer C (2004) PhD thesis, University of RegensburgGoogle Scholar
  111. 111.
    Bonauer C, König B (2005) Synthesis 2367Google Scholar
  112. 112.
    Bonauer C, Zabel M, König B (2004) Org Lett 6:1349Google Scholar
  113. 113.
    Evans DA, Peterson GS, Johnson JS, Barnes DM, Campos KR, Woerpel KA (1998) J Org Chem 63:4541 workup changedGoogle Scholar
  114. 114.
    Fife TH, Przystas TJ (1982) J Am Chem Soc 104:2251Google Scholar
  115. 115.
    Fornasier R, Milani D, Scrimin P, Tonellato U (1986) J Chem Soc Perkins Trans II 233Google Scholar
  116. 116.
    Mansuy D, Fontecave M, Bartoli JF (2003) J Am Chem Soc, Chem Commun 68(24):9419Google Scholar

Copyright information

© Springer-Verlag 2011

Authors and Affiliations

  • Andreas Späth
    • 1
  • Janina Gonschor
    • 1
  • Burkhard König
    • 1
  1. 1.Institut für Organische ChemieUniversität RegensburgRegensburgGermany

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