Synthesis of Enantiomerically Pure 1-Amino-2-phenylcycloalkanecarboxylic Acids (cnPhe)

Marta Lasa; Carlos Cativiela

doi:10.1055/s-2006-951468

ACCOUNT

Synthesis of Enantiomerically Pure 1-Amino-2-phenylcycloalkanecarboxylic Acids (c_nPhe)

Marta Lasa, Carlos Cativiela*
Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza - CSIC, 50009 Zaragoza, Spain
Fax: +34(976)761210; e-Mail: cativiela@unizar.es;

Abstract

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Abstract

Constrained amino acids have become very important tools for modern drug discovery research. Phenylalanine is an appropriate residue for study, due to its participation in active site recognition. The series of 1-amino-2-phenylcycloalkanecarboxylic acids - c_nPhe - constitutes an attractive family of constrained analogues of phenylalanine that can provide different orientations of the phenyl moiety. All stereoisomers of this series, from the cyclopropane to the cyclohexane members, are available in enantiomerically pure form.

1 Introduction

2 Synthesis of Enantiomerically Pure c_nPhe Surrogates

2.1 Synthesis of All Stereoisomers of 1-Amino-2-phenylcyclopropanecarboxylic Acid (c₃Phe)

2.2 Synthesis of All Stereoisomers of 1-Amino-2-phenylcyclobutanecarboxylic Acid (c₄Phe)

2.3 Synthesis of All Stereoisomers of 1-Amino-2-phenylcyclopentanecarboxylic Acid (c₅Phe)

2.4 Synthesis of All Stereoisomers of 1-Amino-2-phenylcyclohexanecarboxylic Acid (c₆Phe)

3 Conclusion

Key words

amino acids - asymmetric synthesis - enantiomeric resolution - peptides

Full Text

References

<A NAME="RA42206ST-1A">1a</A> Hruby VJ. Balse PM. Curr. Med. Chem. 2000, 7: 945

<A NAME="RA42206ST-1B">1b</A> Cowell SM. Lee YS. Cain JP. Hruby VJ. Curr. Med. Chem. 2004, 11: 2785

<A NAME="RA42206ST-1C">1c</A> Sagan S. Karoyan P. Lequin O. Chassaing G. Lavielle S. Curr. Med. Chem. 2004, 11: 2799

<A NAME="RA42206ST-2">2</A> Ramachandran GN. Sasisekharan V. Adv. Protein Chem. 1968, 23: 283

<A NAME="RA42206ST-3">3</A> Hruby VJ. Li G. Haskell-Luevano C. Shenderovich MD. Biopolymers 1997, 43: 219

<A NAME="RA42206ST-4A">4a</A> Marshall GR. Curr. Opin. Struct. Biol. 1992, 2: 904

<A NAME="RA42206ST-4B">4b</A> Gibson SE. Guillo N. Tozer MJ. Tetrahedron 1999, 55: 585

<A NAME="RA42206ST-5A">5a</A> Avenoza A. Busto JH. Canal N. Peregrina JM. Chem. Commun. 2003, 1376

<A NAME="RA42206ST-5B">5b</A> Avenoza A. Busto JH. Peregrina JM. Pérez-Fernández M. Tetrahedron 2005, 61: 4165

<A NAME="RA42206ST-6A">6a</A> Kimura H. Stammer CH. Shimohigashi Y. Ren-Lin C. Stewart J. Biochem. Biophys. Res. Commun. 1983, 115: 112

<A NAME="RA42206ST-6B">6b</A> Mapelli C. Kimura H. Stammer CH. Int. J. Pept. Protein Res. 1986, 28: 347

<A NAME="RA42206ST-6C">6c</A> Shimohigashi Y. Costa T. Pfeiffer A. Herz A. Kimura H. Stammer CH. FEBS Lett. 1987, 222: 71

<A NAME="RA42206ST-6D">6d</A> Shimohigashi Y. Takano Y. Kamiya H. Costa T. Herz A. Stammer CH. FEBS Lett. 1988, 233: 289

<A NAME="RA42206ST-7">7</A> Mapelli C. Stammer CH. Lok S. Mierke DF. Goodman M. Int. J. Pept. Protein Res. 1988, 32: 484

<A NAME="RA42206ST-8A">8a</A> Ogawa T. Yoshitomi H. Kodama H. Waki M. Stammer CH. Shimohigashi Y. FEBS Lett. 1989, 250: 227

<A NAME="RA42206ST-8B">8b</A> Ogawa T. Shimohigashi Y. Yoshitomi H. Sakamoto H. Kodama H. Waki M. Stammer CH. Pept. Chem. 1989, 26: 25

<A NAME="RA42206ST-9A">9a</A> Yoshitomi H. Shimohigashi Y. Matsumoto H. Waki M. Takano Y. Kamiya H. Stammer CH. Pept. Chem. 1989, 26: 43

<A NAME="RA42206ST-9B">9b</A> Déry O. Josien H. Grassi J. Chassaing G. Couraud JY. Lavielle S. Biopolymers 1996, 39: 67

<A NAME="RA42206ST-10">10</A> Varughese KI. Wang CH. Kimura H. Stammer CH. Int. J. Pept. Protein Res. 1988, 31: 299

<A NAME="RA42206ST-11">11</A> Burgess K. Ho K.-K. Pal B. J. Am. Chem. Soc. 1995, 117: 3808

<A NAME="RA42206ST-12A">12a</A> Jiménez AI. Vanderesse R. Marraud M. Aubry A. Cativiela C. Tetrahedron Lett. 1997, 38: 7559

<A NAME="RA42206ST-12B">12b</A> Jiménez AI. Cativiela C. Aubry A. Marraud M. J. Am. Chem. Soc. 1998, 120: 9452

<A NAME="RA42206ST-13A">13a</A> Avenoza A. París M. Peregrina JM. Alías M. López MP. García JI. Cativiela C. Tetrahedron 2002, 58: 4899

<A NAME="RA42206ST-13B">13b</A> Alías M. Lasa M. López P. García JI. Cativiela C. Tetrahedron 2005, 61: 2913

<A NAME="RA42206ST-14A">14a</A> Jiménez AI. Cativiela C. París M. Peregrina JM. Avenoza A. Aubry A. Marraud M. Tetrahedron Lett. 1998, 39: 7841

<A NAME="RA42206ST-14B">14b</A> Jiménez AI. Cativiela C. Gómez-Catalán J. Pérez JJ. Aubry A. París M. Marraud M. J. Am. Chem. Soc. 2000, 122: 5811

<A NAME="RA42206ST-14C">14c</A> Gómez-Catalán J. Jiménez AI. Cativiela C. Pérez JJ. J. Pept. Res. 2001, 57: 435

<A NAME="RA42206ST-14D">14d</A> Lasa M. Jiménez AI. Zurbano MM. Cativiela C. Tetrahedron Lett. 2005, 46: 8377

<A NAME="RA42206ST-15">15</A> Cativiela C. Díaz-de-Villegas MD. Tetrahedron: Asymmetry 1998, 9: 3517

<A NAME="RA42206ST-16A">16a</A> Cativiela C. Díaz-de-Villegas MD. Tetrahedron: Asymmetry 2000, 11: 645

<A NAME="RA42206ST-16B">16b</A> Park K.-H. Kurth MJ. Tetrahedron 2002, 58: 8629

<A NAME="RA42206ST-17">17</A> Turner NJ. Curr. Org. Chem. 1997, 1: 21

Some recent examples:

<A NAME="RA42206ST-18A">18a</A> Kirihara M. Kawasaki M. Takuwa T. Kahuda H. Wakikawa T. Takeuchi Y. Kirk KL. Tetrahedron: Asymmetry 2003, 14: 1753

<A NAME="RA42206ST-18B">18b</A> Beaulieu PL. Gillard J. Bailey MD. Boucher C. Duceppe J.-S. Simoneau B. Wang X.-J. Zhang L. Grozinger K. Houpis I. Farina V. Heimroth H. Krueger T. Schnaubelt J. J. Org. Chem. 2005, 70: 5869

<A NAME="RA42206ST-19A">19a</A> Stammer CH. Tetrahedron 1990, 46: 2231

<A NAME="RA42206ST-19B">19b</A> Alami A. Calmes M. Daunis J. Jacquier R. Bull. Soc. Chim. Fr. 1993, 130: 5

<A NAME="RA42206ST-19C">19c</A> Burgess K. Ho K.-K. Moye-Sherman D. Synlett 1994, 575

<A NAME="RA42206ST-20">20</A> Salaün J. Top. Curr. Chem. 2000, 207: 1

<A NAME="RA42206ST-21">21</A> King SW. Riordan JM. Holt EM. Stammer CH. J. Org. Chem. 1982, 47: 3270

<A NAME="RA42206ST-22A">22a</A> Arenal I. Bernabé M. Fernández-Álvarez E. Izquierdo ML. Penadés S. J. Heterocycl. Chem. 1983, 20: 607

<A NAME="RA42206ST-22B">22b</A> Arenal I. Bernabé M. Fernández-Álvarez E. Penadés S. Synthesis 1985, 773

<A NAME="RA42206ST-23">23</A> Bernabé M. Cuevas O. Fernández-Álvarez E. Synthesis 1977, 191

<A NAME="RA42206ST-24A">24a</A> Arenal I. Bernabé M. Fernández-Álvarez E. Hernández-Perretta R. An. Quim. 1981, 77: 93

<A NAME="RA42206ST-24B">24b</A> Arenal I. Bernabé M. Fernández-Álvarez E. Izquierdo ML. An. Quim. 1984, 80: 127

<A NAME="RA42206ST-25">25</A> Izquierdo ML. Arenal I. Bernabé M. Fernández-Álvarez E. Tetrahedron 1985, 41: 215

<A NAME="RA42206ST-26">26</A> Hiyama T. Kai M. Tetrahedron Lett. 1982, 23: 2103

<A NAME="RA42206ST-27">27</A> Spadoni G. Balsamini C. Bedini A. Mugnaini M. Farmaco 1993, 48: 1663

<A NAME="RA42206ST-28">28</A> Cativiela C. Díaz-de-Villegas MD. Jiménez AI. Tetrahedron 1994, 50: 9157

<A NAME="RA42206ST-29">29</A> Adams LA. Aggarwal VK. Bonnert RV. Bressel B. Cox RJ. Shepherd J. de Vicente J. Walter M. Whittingham WG. Winn CL. J. Org. Chem. 2003, 68: 9433

<A NAME="RA42206ST-30">30</A> Charette AB. Wurz RP. Ollevier T. Helv. Chim. Acta 2002, 85: 4468

<A NAME="RA42206ST-31">31</A> Wurz RP. Charette AB. Org. Lett. 2003, 5: 2327

<A NAME="RA42206ST-32">32</A> Wurz RP. Charette AB. J. Org. Chem. 2004, 69: 1262

<A NAME="RA42206ST-33A">33a</A> Fernández MD. Frutos MP. Marco JL. Fernández-Álvarez E. Bernabé M. Tetrahedron Lett. 1989, 30: 3101

<A NAME="RA42206ST-33B">33b</A> Alcaraz C. Fernández MD. Frutos MP. Marco JL. Bernabé M. Foces-Foces C. Cano FH. Tetrahedron 1994, 50: 12443

<A NAME="RA42206ST-34">34</A> Williams RM. Fegley GJ. J. Am. Chem. Soc. 1991, 113: 8796

<A NAME="RA42206ST-35">35</A> Williams RM. Fegley GJ. J. Org. Chem. 1993, 58: 6933

<A NAME="RA42206ST-36">36</A> Aggarwal VK. Alonso E. Fang G. Ferrara M. Hynd G. Porcelloni M. Angew. Chem. Int. Ed. 2001, 40: 1433

<A NAME="RA42206ST-37">37</A> Davies HML. Clark TJ. Church LA. Tetrahedron Lett. 1989, 30: 5057

<A NAME="RA42206ST-38">38</A> Davies HML. Cantrell WR. Tetrahedron Lett. 1991, 32: 6509

<A NAME="RA42206ST-39">39</A> Davies HML. Huby NJS. Cantrell WR. Olive JL. J. Am. Chem. Soc. 1993, 115: 9468

<A NAME="RA42206ST-40">40</A> Davies HML. Hutcheson DK. Tetrahedron Lett. 1993, 34: 7243

<A NAME="RA42206ST-41">41</A> Davies HML. Kong N. Tetrahedron Lett. 1997, 38: 4203

<A NAME="RA42206ST-42">42</A> Davies HML. Bruzinski PR. Lake DH. Kong N. Fall MJ. J. Am. Chem. Soc. 1996, 118: 6897

<A NAME="RA42206ST-43">43</A> Charette AB. Wurz R. J. Mol. Catal. A: Chem. 2003, 196: 83

<A NAME="RA42206ST-44">44</A> Moreau B. Charette AB. J. Am. Chem. Soc. 2005, 127: 18014

<A NAME="RA42206ST-45">45</A> Kimura H. Stammer CH. J. Org. Chem. 1983, 48: 2440

<A NAME="RA42206ST-46">46</A> Mapelli C. Kimura H. Stammer CH. Int. J. Pept. Protein Res. 1986, 28: 347

<A NAME="RA42206ST-47">47</A> Cativiela C. Díaz-de-Villegas MD. Jiménez AI. López P. Marraud M. Oliveros L. Chirality 1999, 11: 583

<A NAME="RA42206ST-48A">48a</A> Dingenen J. In A Practical Approach to Chiral Separations by Liquid Chromatography Subramanian G. VCH; Weinheim: 1994. p.115

<A NAME="RA42206ST-48B">48b</A> Yashima E. Yamamoto C. Okamoto Y. Synlett 1998, 344

<A NAME="RA42206ST-48C">48c</A> Yamamoto C. Okamoto Y. Bull. Chem. Soc. Jpn. 2004, 77: 227

<A NAME="RA42206ST-49A">49a</A> Oliveros L. López P. Minguillón C. Franco P. J. Liq. Chromatogr. 1995, 18: 1521

<A NAME="RA42206ST-49B">49b</A> Minguillón C. Franco P. Oliveros L. López P. J. Chromatogr., A 1996, 728: 407

<A NAME="RA42206ST-50A">50a</A> Beard C. Burger A. J. Org. Chem. 1961, 26: 2335

<A NAME="RA42206ST-50B">50b</A> Burger A. Coyne WE. J. Org. Chem. 1964, 29: 3079

<A NAME="RA42206ST-50C">50c</A> Burger A. inventors; US 3 345 405. ; Chem. Abstr. 1968, 68, 49173b

<A NAME="RA42206ST-51">51</A> Truong M. Lecornué F. Fadel A. Tetrahedron: Asymmetry 2003, 14: 1063

<A NAME="RA42206ST-52">52</A> Lasa M. López P. Cativiela C. Tetrahedron: Asymmetry 2005, 16: 4022

<A NAME="RA42206ST-53">53</A> Burckhalter JH. Schmied G. J. Pharm. Sci. 1966, 55: 443

<A NAME="RA42206ST-54">54</A> Trost BM. Dogra K. J. Am. Chem. Soc. 2002, 124: 7256

<A NAME="RA42206ST-55">55</A> Cativiela C. Lasa M. López P. Tetrahedron: Asymmetry 2005, 16: 2613

<A NAME="RA42206ST-56">56</A> Cativiela C. Díaz-de-Villegas MD. Avenoza A. Peregrina JM. Tetrahedron 1993, 49: 10987

<A NAME="RA42206ST-57">57</A> Cativiela C. López P. Lasa M. Eur. J. Org. Chem. 2004, 3898

<A NAME="RA42206ST-58">58</A> Cantarelli G. Carissimi M. Ravenna F. Riva G. Farmaco 1975, 30: 761

<A NAME="RA42206ST-59">59</A> Sacripante G. Edward JT. Can. J. Chem. 1982, 60: 1982

<A NAME="RA42206ST-60">60</A> Cativiela C. Avenoza A. París M. Peregrina JM. J. Org. Chem. 1994, 59: 7774

<A NAME="RA42206ST-61">61</A> Hartmann H. Hady AFA. Sator K. Weetman J. Helmchen G. Angew. Chem., Int. Ed. Engl. 1987, 26: 1143

<A NAME="RA42206ST-62">62</A> Alías M. Cativiela C. Jiménez AI. López P. Oliveros L. Marraud M. Chirality 2001, 13: 48

<A NAME="RA42206ST-63">63</A> Avenoza A. Busto JH. Cativiela C. Peregrina JM. Rodríguez F. Tetrahedron 1998, 54: 11659

<A NAME="RA42206ST-64">64</A> Obrecht D. Splieger C. Schönholzer P. Müller K. Helv. Chim. Acta 1992, 75: 1666

Synthesis of Enantiomerically Pure 1-Amino-2-phenylcycloalkanecarboxylic Acids (c n Phe)

Synthesis of Enantiomerically Pure 1-Amino-2-phenylcycloalkanecarboxylic Acids (c_nPhe)