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Synthesis 2009(18): 3136-3142  
DOI: 10.1055/s-0029-1217602
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Functionalized l-Cysteine and l-Methionine by Reaction with Electron-Deficient Acetylenes

Boris A. Trofimov*, Anastasiya G. Mal’kina, Olesya A. Shemyakina, Valentina V. Nosyreva, Angela P. Borisova, Spartak S. Khutsishvili, Leonid B. Krivdin
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;
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Publikationsverlauf

Received 28 April 2009
Publikationsdatum:
10. Juli 2009 (online)

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Abstract

A novel families of nonconventionally functionalized amino acids have been synthesized in almost quantitative yields by chemo-, regio- and stereospecific addition of l-cysteine and l-­methionine to electron-deficient functionalized acetylenes (cyano-acetylenes and methyl 4-hydroxy-4-methylpent-2-ynoate) under mild conditions (water, r.t., 2-5 h). Thus, for the first time, the uncommonly functionalized optically active amino acids composing of l-cysteine and l-methionine structural units along with cinnamic acid, dihydrofuranone, iminodihydrofuran, and other biologically important functionalities are readily available.

Key words

alkynes - amino acids - nucleophilic addition - cyclization

    References

  • 1a Twyman RM. Principles of Proteomics   BIOS Scientific; New York: 2004. 
  • 1b Zhao L. Li C.-J. Angew. Chem. Int. Ed.  2008,  47:  7075 
    Suche in Google Scholar
  • 2a Seebach D. Beck AK. Studer A. In Modern Synthetic Methods   Vol. 7:  Ernst B. Leumann C. VCH; Weinheim: 1995.  p.1 
    Suche in Google Scholar
  • 2b Kotha S. Lahiri K. Bioorg. Med. Chem. Lett.  2001,  11:  2887 
    Suche in Google Scholar
  • 3a Pillai O. Panchagnula R. Drug Discovery Today  2001,  6:  1056 
    Suche in Google Scholar
  • 3b Carrell RW. Lomas DA. Lancet  1997,  350:  134 
    Suche in Google Scholar
  • 3c Cochran AG. Chem. Biol.  2000,  7:  R85 
    Suche in Google Scholar
  • 3d van Hest JCM. Tirrel DA. Chem. Commun.  2001,  1897 
  • 4 Wang X. Guo Z. Anticancer Agents Med. Chem.  2007,  7:  19 
    CrossrefSuche in Google Scholar
  • 5a Drabkin HJ. RajBhandary UL. Mol. Cell. Biol.  1998,  18:  5140 
    Suche in Google Scholar
  • 5b Brosnan JT. Brosnan ME. J. Nutr.  2006,  136:  1636S 
    Suche in Google Scholar
  • 6a Zhou NE. Reddy AVN. Kaleta J. Micetich RG. Singh R. ARKIVOC  2001,  (vi):  116 
    Suche in Google Scholar
  • 6b Mashkovskii MD. Drugs (in Russian)   Novaya Volna; Moscow: 2003. 
  • 6c Hsu C.-C. Huang C.-N. Hung Y.-C. Yin M.-C. J. Nutr.  2004,  134:  149 
    Suche in Google Scholar
  • 6d Ali V. Nozaki T. Clinical Microbiol. Rev.  2007,  164 ; and references cited therein
  • 6e Oda H. J. Nutr.  2006,  136:  1666S 
    Suche in Google Scholar
  • 7 Riedijk MA. Stoll B. Chacko S. Schierbeek H. Sunehag AL. van Goudoever JB. Burrin DG. Proc. Natl. Acad. Sci. U.S.A.  2007,  104:  3408 
    CrossrefSuche in Google Scholar
  • 8 Enevoldsen T. Oddershede J. Sauer SPA. Theor. Chem. Acc.  1998,  100:  275 
    CrossrefSuche in Google Scholar
  • 9 Provasi PF. Aucar GA. Sauer SPA. J. Chem. Phys.  2001,  115:  1324 
    CrossrefSuche in Google Scholar
  • 10 Woon DE. Dunning TH. J. Chem. Phys.  1995,  103:  4572 
    CrossrefSuche in Google Scholar
  • 11 Sauer SPA. Krivdin LB. Magn. Reson. Chem.  2004,  42:  671 
    CrossrefSuche in Google Scholar
  • 12 Angeli C. Bak KL. Bakken V. Christiansen O. Cimiraglia R. Coriani S. Dahle P. Dalskov EK. Enevoldsen T. Fernandez B. Haettig C. Hald K. Halkier A. Heiberg H. Helgaker T. Hettema H. Jensen HJA. Jonsson D. Joergensen P. Kirpekar S. Klopper W. Kobayashi R. Koch H. Ligabue A. Lutnaes OB. Mikkelsen KV. Norman P. Olsen J. Packer MJ. Pedersen TB. Rinkevicius Z. Rudberg E. Ruden TA. Ruud K. Salek P. Sanchez de Meras A. Saue T. Sauer SPA. Schimmelpfennig B. Sylvester-Hvid KO. Taylor PR. Vahtras O. Wilson DJ. Ågren H. Dalton: A Molecular Electronic Structure Program  2005,  Release 2.0; http://www.kjemi.uio.no/software/dalton/dalton.html
  • 13 Schmidt MW. Baldridge KK. Boatz JA. Elbert ST. Gordon MS. Jensen JH. Koseki S. Matsunaga N. Nguyen KA. Su SJ. Windus TL. Dupuis M. Montgomery JA. J. Comput. Chem.  1993,  14:  1347 
    CrossrefSuche in Google Scholar
  • 14 Silverstein R. Bassler G. Morril T. Spectrometric Identification of Organic Compounds   Wiley; New York: 1974. 
  • 15a Miller SI. Tanaka R. In Selective Organic Transformation   Vol. 1:  Thyagarajan BS. Wiley-Interscience; New York: 1970.  p.143 
    Suche in Google Scholar
  • 15b Dickstein JI. Miller SI. In The Chemistry of the Carbon-Carbon Triple Bond   Part 2:  Patai S. Wiley; New York: 1978.  p.814 
    Suche in Google Scholar
  • 16 Tahir H. Hindsgaul O. J. Org. Chem.  2000,  65:  911 
    CrossrefSuche in Google Scholar
  • 17a Effenberger F. Syed J. Tetrahedron: Asymmetry  1998,  9:  817 
    Suche in Google Scholar
  • 17b Shenoy G. Kim P. Goodwin M. Nguyen Q.-A. Barry CE. Dowd CS. Heterocycles  2004,  63:  519 
    Suche in Google Scholar
  • 17c Rajaram AR. Pu L. Org. Lett.  2006,  8:  2019 
    Suche in Google Scholar
  • 17d Zografos AI. Georgiadis D. Synthesis  2006,  3157 
  • 18a Gao WY. Agbaria R. Driscoll JS. Mitsuya H. J. Biol. Chem.  1994,  269:  12633 
    Suche in Google Scholar
  • 18b Meier C. Synlett  1998,  233 
  • 18c Saboulard D. Naesens L. Cahard D. Salgado A. Pathirana R. Velazquez S. Mcguigan Ch. De Clercq E. Balzarin J. Mol. Pharmacol.  1999,  56:  693 
    Suche in Google Scholar
  • 18d Bradshaw PC. Li J. Samuels DC. Biochem. J.  2005,  392:  363 
    Suche in Google Scholar
  • 19 Lichtenthaler FW. Cuny E. Sakanaka O. Angew. Chem. Int. Ed.  2005,  44:  4944 ; Angew. Chem. 2005, 117, 5024
    CrossrefSuche in Google Scholar
  • 20a Gunasekera SP. McCarthy PJ. Kelly-Borges M. J. Am. Chem. Soc.  1996,  118:  8759 
    Suche in Google Scholar
  • 20b Corey EJ. Roberts BE. J. Am. Chem. Soc.  1997,  119:  12425 
    Suche in Google Scholar
  • 20c Takahashi M. Dodo K. Sugimoto Y. Aoyagi Y. Yamada Y. Hasimoto Y. Shirai R. Bioorg. Med. Chem. Lett.  2000,  10:  2571 
    Suche in Google Scholar
  • 20d Miyaoka H. Kajiwara Y. Hara Y. Yamada Y. J. Org. Chem.  2001,  66:  1429 
    Suche in Google Scholar
  • 20e Brohm D. Philippe N. Metzger S. Bhargava A. Muller O. Lieb F. Waldmann H. J. Am. Chem. Soc.  2002,  124:  13171 
    Suche in Google Scholar
  • 21a Soriente A. Crispino A. De Rosa M. De Rosa S. Scettri A. Scognamiglio G. Villano R. Sodano G. Eur. J. Org. Chem.  2000,  943 
  • 21b Basabe P. Delgado S. Marcos IS. Diez D. Diego A. De Roman M. Urones JG. J. Org. Chem.  2005,  70:  9480 
    Suche in Google Scholar
  • 22a Mangnus EM. Stommen PLA. Zwanenburg B. J. Plant Growth Regul.  1992,  11:  91 
    Suche in Google Scholar
  • 22b Kuad P. Borkovec M. Murr MD.-E. Le Gall T. Mioskowski Ch. Spiess B. J. Am. Chem. Soc.  2005,  127:  1323 
    Suche in Google Scholar
  • 23a Mangnus EM. Zwanenburg B. J. Agric. Food Chem.  1992,  40:  1066 
    Suche in Google Scholar
  • 23b Thuring JWJF. van Gaal AAMA. Hornes SJ. de Kok MM. Nefkens GHL. Zwanenburg B. J. Chem. Soc., Perkin Trans. 1  1997,  767 
  • 24 Trofimov BA. Mal’kina AG. Shemyakina OA. Borisova AP. Nosyreva VV. Dyachenko OA. Kazheva ON. Alexandrov GG. Synthesis  2007,  2641 
    Thieme Connect
  • 25 Skvortsov YuM. Mal’kina AG. Volkov AN. Trofimov BA. Oleinikova EB. Kazin IV. Gedymin VV. Izv. Akad. Nauk SSSR, Ser. Khim.  1978,  872 ; Chem. Abstr. 1978, 89, 24231q
  • 26a Landor SR. Demetriou B. Grzeskowiak R. Pavey D. J. Organomet. Chem.  1975,  93:  129 
    Suche in Google Scholar
  • 26b Trofimov BA. Andriyankova LV. Shaikhudinova SI. Kazantseva TI. Mal’kina AG. Zhivet’ev SA. Afonin AV. Synthesis  2002,  853 
  • 27a Trofimov BA. Skvortsov YuM. Mal’kina AG. Gritsa AI. Zh. Org. Khim.  1985,  21:  2020 ; Chem. Abstr. 1986, 105, 78491s
    Suche in Google Scholar
  • 27b Trofimov BA. Mal’kina AG. Gritsa AI. Skvortsov YuM. Stankevich VK. Sokolyanskaya LV. Zh. Obshch. Khim.  1996,  66:  106 ; Chem. Abstr. 1997, 126, 18567v
    Suche in Google Scholar