Synthesis 2010(18): 3174-3178  
DOI: 10.1055/s-0030-1257912
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Chemo- and Regiospecific Modification of d,l-Tryptophan by Reaction with α,β-Acetylenic γ-Hydroxy Nitriles

Boris A. Trofimov*, Anastasiya G. Mal’kina, Angela P. Borisova, Olesya A. Shemyakina, Valentina V. Nosyreva, Alexander I. Albanov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033, Irkutsk, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;
Weitere Informationen

Publikationsverlauf

Received 28 April 2010
Publikationsdatum:
04. August 2010 (online)

Abstract

d,l-Tryptophan reacts with α,β-acetylenic γ-hydroxy nitriles, chemo- and regiospecifically, under mild, green conditions via a hydroamination-type process involving the primary amine group. The hydroxycyanopropanyl substituent of the initial adducts undergoes cyclization to afford a 2,5-dihydro-5-iminofuranyl moiety. Several novel amino acids are obtained in almost quantitative yields (95-98%), which exist in an unusual zwitterionic form where the positive charge is located on the remote nitrogen atom of the imino group of the dihydrofuran ring.

    References

  • 1a Gul W. Hamann MT. Life Sci.  2005,  78:  442 
  • 1b Humphrey GR. Kuethe JT. Chem. Rev.  2006,  106:  2875 
  • 1c Tanimori S. Ura H. Kirihata M. Eur. J. Org. Chem.  2007,  3977 
  • 1d de Sá Alves FR. Barreiro EJ. Fraga CAM. Mini Rev. Med. Chem.  2009,  9:  782 
  • 2a Sundberg RJ. The Chemistry of Indoles   Academic Press; New York: 1970. 
  • 2b Brown RK. In Indoles   Houlihan WJ. Wiley-Interscience; New York: 1972. 
  • 2c Sundberg RJ. Pyrroles and Their Benzo Derivatives: Synthesis and Applications, In Comprehensive Heterocyclic Chemistry   Vol. 4:  Katritzky AR. Rees CW. Pergamon; Oxford: 1984.  p.313-376  
  • 2d Sundberg RJ. Indoles (Best Synthetic Methods Key Systems and Functional Groups)   Academic Press; New York: 1996.  p.7-11  
  • 2e Sundberg RJ. In Comprehensive Heterocyclic Chemistry II   Vol. 2:  Katritzky AR. Rees CW. Scriven EFV. Bird CW. Pergamon Press; Oxford: 1996.  p.119 
  • 2f Gribble GW. In Comprehensive Heterocyclic Chemistry II   Vol. 2:  Katritzky AR. Rees CW. Scriven EFV. Bird CW. Pergamon Press; Oxford: 1996.  p.207 
  • 2g Indoles   Sundberg RJ. Academic Press; London: 1996. 
  • 2h Sundberg RJ. The Chemistry of Indoles   Academic Press; San Diego: 1997.  p.267 
  • 2i Joule JA. Indole and its Derivatives, In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations   Vol. 10:  Thomas EJ. George Thieme Verlag; Stuttgart: 2000.  Chap. 10.13.
  • 3a Evans BE. Rittle KE. Bock MG. DiPardo RM. Freidinger RM. Whitter WL. Lundell GF. Verber DF. Anderson PS. Chang RSL. Lotti VJ. Cerino DJ. Chen TB. Kling PJ. Kunkel KA. Springer JP. Hirshfield J. J. Med. Chem.  1988,  31:  2235 
  • 3b Ohba H. Yamasaki N. Funatsu G. Agric. Biol. Chem.  1991,  55:  1579 
  • 3c Carlier PR. Lam PC.-H. Wong DM. J. Org. Chem.  2002,  67:  6256 
  • 3d Horton DA. Bourne GT. Smythe ML. Chem. Rev.  2003,  103:  893 ; and references cited therein
  • 3e de la Herrán G. Segura A. Csákÿ AG. Org. Lett.  2007,  9:  961 
  • 4 Conigrave AD. Quinn SJ. Brown EM. Proc. Natl. Acad. Sci. U.S.A.  2000,  97:  4814 
  • 5a Friedman M. Cug J.-L. J. Agric. Food Chem.  1988,  36:  1079 
  • 5b Lee DG. Cho NJ. Choi JD. J. Biochem. Mol. Biol.  1996,  29:  321 
  • 5c Murch SJ. KrishnaRaj S. Saxena PK. Plant Cell Rep.  2000,  19:  698 
  • 5d Hirasawa M. Nakayama M. Kim S.-K. Hase T. Knaff DB. Photosynth. Res.  2005,  86:  325 
  • 5e Bender J. Celenza JL. Phytochem Rev.  2009,  8:  25 
  • 6 Somei M, Hattori A, and Suzuki N. inventors; WO 2007010723,  .  (National University Corporation, Kanazawa University, Japan, National University Corporation, Tokyo Medical and Dental University, Japan) ; Chem. Abstr. 2007, 146, 163392
  • 7 Walther D, and Bader M. inventors; WO  2002074309.  , (Max-Delbruck-Centrum fuer Moleculare Medizin, Germany) ; Chem. Abstr. 2002, 137, 242150
  • 8 Watanabe F. inventors; US  6727266.  , (Shionogi and Co., Ltd., Japan) ; Chem. Abstr. 2001, 135, 137709
  • 9a Ybarra J. Prasad ARS. Nishimura JS. Biochemistry  1986,  25:  7174 
  • 9b Tsubota T. Hagiwara Y. Murakami N. Ohno T. Diamond Relat. Mater.  2009,  18:  1174 
  • 10 Stachel SJ. Habeeb RL. Van Vranken DL. J. Am. Chem. Soc.  1996,  118:  1225 
  • 11a Seradj H. Cai W. Erasga NO. Chenault DV. Knuckles KA. Ragains JR. Behforouz M. Org. Lett.  2004,  6:  473 
  • 11b Hassani M. Cai W. Holley DC. Lineswala JP. Maharjan BR. Ebrahimian GR. Seradj H. Stocksdale MG. Mohammadi F. Marvin CC. Gerdes JM. Beall HD. Behforouz M. J. Med. Chem.  2005,  48:  7733 
  • 11c Liu J. Cui G. Zhao M. Cui C. Jub J. Peng S. Bioorg. Med. Chem.  2007,  15:  7773 
  • 12 Sakiyan I. Logoglu E. Arslan S. Sari N. Sakiyan N. BioMetals  2004,  17:  115 
  • 13a Skvortsov YM. Mal’kina AG. Trofimov BA. Zh. Org. Khim.  1983,  19:  1351 
  • 13b Skvortsov YM. Mal’kina AG. Trofimov BA. Kositsyna EI. Voronov VK. Baikalova LV. Zh. Org. Khim.  1984,  20:  1108 
  • 13c Trofimov BA. Mal’kina AG. Skvortsov YM. Zh. Org. Khim.  1993,  29:  1268 
  • 13d Mal’kina AG. Nosyreva VV. Kositsyna EI. Trofimov BA. Zh. Org. Khim.  1997,  33:  449 
  • 13e Trofimov BA. Mal’kina AG. Heterocycles  1999,  51:  2485 
  • 14 Skvortsov YM. Mal’kina AG. Trofimov BA. Volkov AN. Glaskova NP. Proidakov AG. Zh. Org. Khim.  1982,  18:  983 
  • 15 Nosyreva VV. Mal’kina AG. Shemyakina OA. Kositsyna EI. Albanov AI. Trofimov BA. Zh. Org. Khim.  2005,  41:  1225 
  • 16a Trofimov BA. Mal’kina AG. Shemyakina OA. Borisova AP. Nosyreva VV. Dyachenko OA. Kazheva ON. Alexandrov GG. Synthesis  2007,  2641 
  • 16b Trofimov BA. Mal’kina AG. Shemyakina OA. Nosyreva VV. Borisova AP. Khutsishvili SS. Krivdin LB. Synthesis  2009,  3136 
  • 17 Trofimov BA. Mal’kina AG. Shemyakina OA. Nosyreva VV. Borisova AP. Albanov AI. Kazheva ON. Alexandrov GG. Chekhlov AN. Dyachenko OA. Tetrahedron  2009,  65:  2472 
  • 18a Effenberger F. Syed J. Tetrahedron: Asymmetry  1998,  9:  817 
  • 18b Shenoy G. Kim P. Goodwin M. Nguyen Q.-A. Barry CE. Dowd CS. Heterocycles  2004,  63:  519 
  • 18c Rajaram AR. Pu L. Org. Lett.  2006,  8:  2019 
  • 18d Zografos AI. Georgiadis D. Synthesis  2006,  3157 
  • 19 Tahir H. Hindsgaul O. J. Org. Chem.  2000,  65:  911 
  • 20a Gao WY. Agbaria R. Driscoll JS. Mitsuya H.
    J. Biol. Chem.  1994,  269:  12633 
  • 20b Meier C. Synlett  1998,  233 
  • 20c Saboulard D. Naesens L. Cahard D. Salgado A. Pathirana R. Velazquez S. McGuigan C. De Clercq E. Balzarini J. Mol. Pharm.  1999,  56:  693 
  • 20d Bradshaw PC. Li J. Samuels DC. Biochem. J.  2005,  392:  363 
  • 21 Lichtenthaler FW. Cuny E. Sakanaka O. Angew. Chem. Int. Ed.  2005,  44:  4944 ; Angew. Chem. 2005, 117, 5024
  • 22a Gunasekera SP. McCarthy PJ. Kelly-Borges M.
    J. Am. Chem. Soc.  1996,  118:  8759 
  • 22b Corey EJ. Roberts BE. J. Am. Chem. Soc.  1997,  119:  12425 
  • 22c Takahashi M. Dodo K. Sugimoto Y. Aoyagi Y. Yamada Y. Hashimoto Y. Shirai R. Bioorg. Med. Chem. Lett.  2000,  10:  2571 
  • 22d Miyaoka H. Kajiwara Y. Hara Y. Yamada Y. J. Org. Chem.  2001,  66:  1429 
  • 22e Brohm D. Philippe N. Metzger S. Bhargava A. Muller O. Lieb F. Waldmann H. J. Am. Chem. Soc.  2002,  124:  13171 
  • 23a Soriente A. Crispino A. De Rosa M. De Rosa S. Scettri A. Scognamiglio G. Villano R. Sodano G. Eur. J. Org. Chem.  2000,  943 
  • 23b Basabe P. Delgado S. Marcos IS. Diez D. Diego A. De Roman M. Urones JG. J. Org. Chem.  2005,  70:  9480 
  • 24a Mangnus EM. Stommen PLA. Zwanenburg B.
    J. Plant Growth Regul.  1992,  11:  91 
  • 24b Kuad P. Borkovec M. Desage-El Murr M. Le Gall T. Mioskowski C. Spiess B. J. Am. Chem. Soc.  2005,  127:  1323 
  • 25a Mangnus EM. Zwanenburg B. J. Agric. Food Chem.  1992,  40:  1066 
  • 25b Thuring JWJF. van Gaal AAMA. Hornes SJ. de Kok MM. Nefkens GHL. Zwanenburg B. J. Chem. Soc., Perkin Trans. 1  1997,  767 
  • 26a Landor SR. Demetriou B. Grzeskowiak R. Pavey DF. J. Organomet. Chem.  1975,  93:  129 
  • 26b Hopf H. Witulski B. In Modern Acetylene Chemistry   Stang PJ. Diederich F. Wiley-VCH; Weinheim: 1995.  Chap. 2. p.33-67  
  • 26c Trofimov BA. Andriyankova LV. Shaikhudinova SI. Kazantseva TI. Mal’kina AG. Zhivet’ev SA. Afonin AV. Synthesis  2002,  853 
  • 27 Trofimov BA. Curr. Org. Chem.  2002,  6:  1121