Molecular Signal Transduction by Conformational Transmission

Rolf Krauss; Ulrich Koert

doi:10.1055/s-2003-38344

ACCOUNT

Molecular Signal Transduction by Conformational Transmission

Rolf Krauss, Ulrich Koert*
Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße, 35032 Marburg, Germany
Fax: +49(6421)2825677; e-Mail: koert@chemie.uni-marburg.de;

Abstract

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Abstract

2,3,6,7-Tetrasubstituted cis-anti-cis perhydroanthra-cenes and cis-decalines are suitable transducers for molecular signals via conformational transmission. Repeated use of a Lewis-acid catalyzed Diels-Alder reaction led to the stereoselective construction of the perhydroanthracene and decalin target molecules. A covalently induced triple ring flip of the perhydroanthacene system was achieved by the formation of a bisacetal. A chelation induced conformational switch was possible with bipyridine receptor groups in positions 6 and 7 and Zn(II) as the incoming signal. By attaching pyrene effectors in positions 2 and 3 the ability of the device to transduce a molecular signal from the receptor via the biconformational transducer to the effector leading to an outcoming photosignal was proven.

Key words

conformational analysis - molecular switch - perhydroanthracene - signal transduction - stereoselective synthesis

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References

<A NAME="RA27402ST-1">1</A> Krauss G. Biochemistry of Signal Transduction and Regulation Wiley-VCH; Weinheim: 1999.

<A NAME="RA27402ST-2">2</A> Special issue on Photochromism: Memories and Switches: Chem. Rev. 2000, 100: 1683-1890

<A NAME="RA27402ST-3">3</A> Balzani V. Credi A. Mattersteig G. Mathews OA. Raymo FM. Stoddart JF. Venturi M. White AJP. Williams DJJ. Org. Chem. 2000, 65: 1924

<A NAME="RA27402ST-4">4</A> Beer PD. Chem. Soc. Rev. 1989, 18: 409

<A NAME="RA27402ST-5">5</A> Dong T.-Y. Chang C.-K. Cheng C.-H. Lin K.-J. Organometallics 1999, 18: 1911

<A NAME="RA27402ST-6">6</A> Fabbrizzi L. Poggi A. Chem. Soc. Rev. 1995, 24: 197

<A NAME="RA27402ST-7">7</A> Fabbrizzi L. Licchelli M. Pallavicini P. Acc. Chem. Res. 1999, 32: 846

<A NAME="RA27402ST-8">8</A> Hegetschweiler K. Kradolfer T. Gramlich V. Hancock RD. Chem.-Eur. J. 1995, 1: 74

<A NAME="RA27402ST-9">9</A> Hennrich G. Sonnenschein H. Resch-Genger U. J. Am. Chem. Soc. 1999, 121: 5073

<A NAME="RA27402ST-10">10</A> Kawai SH. Gilat SL. Lehn JM. J. Chem. Soc., Chem. Commun. 1994, 1011

<A NAME="RA27402ST-11">11</A> Kradolfer T. Hegetschweiler K. Helv. Chim. Acta 1992, 75: 2243

<A NAME="RA27402ST-12">12</A> Lehn JM. Supramolecular Chemistry VCH; Weinheim: 1995. p.129

<A NAME="RA27402ST-13">13</A> Birau MM. Wang ZY. Tetrahedron Lett. 2000, 41: 4025

<A NAME="RA27402ST-14">14</A> Plenio H. Aberle C. Organometallics 1997, 16: 5950

<A NAME="RA27402ST-15">15</A> Plenio H. Aberle C. Angew. Chem. Int. Ed. 1998, 37: 1397 ; Angew. Chem. 1998, 110, 1467

<A NAME="RA27402ST-16">16</A> Raban M. Burch DL. Hortelano R. Durocher D. Kost D. J. Org. Chem. 1994, 59: 1283

<A NAME="RA27402ST-17">17</A> de Silva AP. Gunaratne HQN. Gunnlaugsson T. Huxley AJM. McCoy CP. Rademacher JT. Rice TE. Chem. Rev. 1997, 97: 1515

<A NAME="RA27402ST-18">18</A> Tsivgoulis GM. Lehn J.-M. Adv. Mater. 1997, 9: 39

<A NAME="RA27402ST-19">19</A> Yuasa H. Hashimoto H. J. Am. Chem. Soc. 1999, 121: 5089

<A NAME="RA27402ST-20">20</A> Balzani V. Gomez-Lopez M. Stoddardt JF. Acc. Chem. Res. 1998, 31: 405

<A NAME="RA27402ST-21">21</A> Balzani V. Credi A. Raymo FM. Stoddart JF. Angew. Chem. Int. Ed. 2000, 39: 3348 ; Angew. Chem. 2000, 112, 3484

<A NAME="RA27402ST-22">22</A> Balzani V. Credi A. Langford SJ. Raymo FM. Stoddart JF. Venturi M. J. Am. Chem. Soc. 2000, 122: 3542

<A NAME="RA27402ST-23">23</A> Raymo FM. Giordani S. J. Am. Chem. Soc. 2001, 123: 4651

<A NAME="RA27402ST-24">24</A> Wittinghofer A. Waldmann H. Angew. Chem. Int. Ed. 2000, 39: 4192 ; Angew. Chem. 2000, 112, 4360

<A NAME="RA27402ST-25">25</A> Ray LB. Science 1999, 284: 755

<A NAME="RA27402ST-26">26</A> Krauss R. Weinig H.-G. Seydack M. Bendig J. Koert U. Angew. Chem. Int. Ed. 2000, 39: 1835 ; Angew. Chem. 2000, 112, 1905

<A NAME="RA27402ST-27">27</A> Koert U. Krauss R. Weinig H.-G. Heumann C. Ziemer B. Mügge C. Seydack M. Bendig J. Eur. J. Org. Chem. 2001, 575

<A NAME="RA27402ST-28">28</A> Weinig H.-G. Krauss R. Seydack M. Bendig J. Koert U. Chem.-Eur. J. 2001, 7: 2075

<A NAME="RA27402ST-29">29</A> Krauss R. Stereoselektive Synthese bikonformationeller Bausteine für Schalter und zur molekularen Signaltransduktion Logos Verlag; Berlin: 2001.

<A NAME="RA27402ST-30">30</A> Barton DHR. Science 1970, 169: 539

<A NAME="RA27402ST-31">31</A> Hoffmann RW. Münster I. Liebigs Ann. Recueil 1997, 1143

<A NAME="RA27402ST-32">32</A> De Oliveira Santos AG. Klute W. Torode J. Böhm VPW. Cabrita E. Runsink J. Hoffmann RW. New. J. Chem. 1998, 993

<A NAME="RA27402ST-33">33</A> Berninger J. Krauss R. Weinig H.-G. Koert U. Ziemer B. Harms K. Eur. J. Org. Chem. 1999, 875

<A NAME="RA27402ST-34">34</A> Hoffmann RW. Angew. Chem. Int. Ed. 2000, 39: 2054 ; Angew. Chem. 2000, 112, 2134

<A NAME="RA27402ST-35">35</A> Eliel EL. Wilen SH. Mander LN. Stereochemistry of Organic Compounds Wiley; New York: 1994.

<A NAME="RA27402ST-36">36</A> Corey EJ. Feiner NF. J. Org. Chem. 1980, 45: 765

<A NAME="RA27402ST-37">37</A> Fürst A. Plattner PA. Helv. Chim. Acta 1949, 32: 275

<A NAME="RA27402ST-38">38</A> Fringuelli F. Minuti L. Pizzo F. Taticchi A. Acta Chem. Scand. 1993, 47: 255

<A NAME="RA27402ST-39">39</A> Sharpless KB. Lauer RF. J. Am. Chem. Soc. 1972, 94: 7154

<A NAME="RA27402ST-40">40</A> Bhalerao UT. Rapoport H. J. Am. Chem. Soc. 1971, 93: 4835

<A NAME="RA27402ST-41">41</A> Stephenson LM. Speth DR. J. Org. Chem. 1979, 44: 4683

<A NAME="RA27402ST-42">42</A> Camps F. Parente CA. Synthesis 1978, 215

<A NAME="RA27402ST-43">43</A> Paulmier C. Selenium Reagents and Intermediates in Organic Synthesis Pergamon Press; New York: 1984. p.353f

<A NAME="RA27402ST-44">44</A> Rabjohn N. Org. React. 1949, 5: 331

<A NAME="RA27402ST-45">45</A> For an excellent review see: Ley SV. Baeschlin DK. Dixon DJ. Foster AC. Ince SJ. Priepke HWM. Reynolds DJ. Chem. Rev. 2001, 101: 53

<A NAME="RA27402ST-46">46</A> Ley SV. Priepke HWM. Warriner SL. Angew. Chem. Int. Ed. 1994, 33: 2290 ; Angew. Chem. 1994, 106: 2410

<A NAME="RA27402ST-47">47</A> Montchamp J.-L. Tian F. Hart ME. Frost JW. J. Org. Chem. 1996, 61: 3897

<A NAME="RA27402ST-48">48</A> Martell AE. Smith RM. Critical Stability Constants Plenum Press; New York: 1982. Vol. 5. p.248-249

<A NAME="RA27402ST-49">49</A> Martell AE. Smith RM. Critical Stability Constants Plenum Press; New York: 1989. Vol. 6: p.276

<A NAME="RA27402ST-50">50</A> Martell AE. Smith RM. Critical Stability Constants Vol. 2: Plenum Press; New York: 1990. p.235-237

<A NAME="RA27402ST-51">51</A> Bilyk A. Harding MM. Turner P. Hambley TW. J. Chem. Soc., Dalton Trans. 1994, 2783

<A NAME="RA27402ST-52">52</A> Bilyk A. Harding MM. J. Chem. Soc., Dalton Trans. 1994, 77

<A NAME="RA27402ST-53">53</A> Harding MM. Koert U. Lehn J.-M. Marquis-Rigault A. Piguet C. Siegel J. Helv. Chim. Acta 1991, 74: 594

<A NAME="RA27402ST-54">54</A> Kaes C. Katz A. Hosseini MW. Chem. Rev. 2000, 100: 3553

<A NAME="RA27402ST-55">55</A> Yamasaki K. Yasuda M. J. Am. Chem. Soc. 1956, 78: 1324

<A NAME="RA27402ST-56">56</A> Williamson W. Justus Liebigs Ann. Chem. 1851, 77: 37

<A NAME="RA27402ST-57">57</A> Mancuso AJ. Swern D. Synthesis 1981, 165

<A NAME="RA27402ST-58">58</A> For a review see: Maryanoff BE. Reitz AB. Chem. Rev. 1989, 89: 863

<A NAME="RA27402ST-59">59</A> Martell AE. Smith RM. Critical Stability Constants Vol. 5: Plenum Press; New York: 1982. p.234

<A NAME="RA27402ST-60">60</A> Martell AE. Smith RM. Critical Stability Constants Vol. 1: Plenum Press; New York: 1989. p.367

<A NAME="RA27402ST-61">61</A> Martell AE. Smith RM. Critical Stability Constants Vol. 1: Plenum Press; New York: 1990. p.377-380

<A NAME="RA27402ST-62">62</A> Martell AE. Smith RM. Critical Stability Constants Vol. 2: Plenum Press; New York: 1990. p.186

<A NAME="RA27402ST-63">63</A> Bad BS. Childens WE. Pinnick HW. Tetrahedron 1981, 37: 2091

<A NAME="RA27402ST-64">64</A> Sisido M. In Advances in Photochemistry Vol. 22: Neckers DC. Volman DV. Bünau GV. Wiley; New York: 1997.

<A NAME="RA27402ST-65">65</A> Mastrangelo JC. Conger BM. Chen SH. Chem. Mater. 1997, 9: 227

<A NAME="RA27402ST-66">66</A> Nishizawa S. Kato Y. Teramae N. J. Am. Chem. Soc. 1999, 121: 9463

<A NAME="RA27402ST-67">67</A> Sahoo D. Narayanaswami V. Kay CM. Ryan RO. Biochemistry 2000, 39: 6594

<A NAME="RA27402ST-68">68</A> Aoki I. Harada T. Sakaki T. Kawahara Y. Shinkai S. J. Chem. Soc., Chem. Commun. 1992, 1341

<A NAME="RA27402ST-69">69</A> Bodenant B. Fages F. Delville M.-H. J. Am. Chem. Soc. 1998, 120: 7511

<A NAME="RA27402ST-70">70</A> Birks JB. Photophysics of Aromatic Molecules Wiley; London: 1970.