Synthesis of New Amino Acids with a 5-Imino-2,5-dihydro-3-furanyl Substituent­ at the Amino Group

Boris A. Trofimov; Anastasiya G. Mal’kina; Olesya A. Shemyakina; Angela P. Borisova; Valentina V. Nosyreva; Oleg A. Dyachenko; Olga N. Kazheva; Gennadii G. Alexandrov

doi:10.1055/s-2007-983819

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Synthesis 2007(17): 2641-2646
DOI: 10.1055/s-2007-983819

PAPER

Synthesis of New Amino Acids with a 5-Imino-2,5-dihydro-3-furanyl Substituent at the Amino Group

Boris A. Trofimov*^a, Anastasiya G. Mal’kina^a, Olesya A. Shemyakina^a, Angela P. Borisova^a, Valentina V. Nosyreva^a, Oleg A. Dyachenko^b, Olga N. Kazheva^b, Gennadii G. Alexandrov^c
^a 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;
^b Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 Academician N. N. Semenov Str., 142432 Chernogolovka, Russian Federation
^c N. S. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninskii Prosp., 119991 Moscow, Russian Federation

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Publication History

Received 10 April 2007
Publication Date:
30 July 2007 (online)

Abstract
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Abstract

Amino acids (glycine, β-alanine, γ-aminobutyric and ε-aminocapronic acids, d,l-valine, and d,l-leucine) react under biomimetic conditions (H₂O, NaOH, pH ˜8.6-9.9, room temperature) smoothly with α,β-acetylenic γ-hydroxyacid nitriles to give a novel family of unnatural amino acids containing a 5-imino-2,5-dihydro-3-furanyl substituent at the amino group, in 61-98% yield. As follows from a single-crystal X-ray analysis of 2-[(5-imino-2,2-dimethyl-2,5-dihydro-3-furanyl)amino]acetic acid, the synthesized amino acids are zwitterions with a protonated imino group in the iminodihydrofuran moiety.

Key words

amino acids - acetylenes - nitriles - 2,5-dihydrofurans - nucleophilic addition

References

1a Mashkovskii MD. Drugs (In Russian) Novaya Volna; Moscow: 2003.

Crossref Google Scholar
1b Kretschmer BD. Schmidt WJ. Kostrzewa RM. Herrera-Marschitz M. Amino Acids 2002, 23: 1

Crossref Google Scholar
2a Jsselstijn MI. Kaiser J. van Delft FL. Schoemaker HE. Rutjes FPJT. Amino Acids 2003, 24: 263

Crossref Google Scholar
2b Burger EC. Tunge JA. J. Am. Chem. Soc. 2006, 128: 10002

Crossref Google Scholar
2c Fülöp F. Martinek TA. Tóth GK. Chem. Soc. Rev. 2006, 35: 323

Crossref Google Scholar
2d Che Y. Marshall GR. J. Med. Chem. 2006, 49: 111

Crossref Google Scholar
2e Barsby T. Warabi K. Sørensen D. Zimmerman WT. Kelly MT. Andersen RJ. J. Org. Chem. 2006, 71: 6031

Crossref Google Scholar
2f Pollini GP. Benetti S. De Risi C. Zanirato V. Chem. Rev. 2006, 106: 2434

Crossref Google Scholar
3a Niece KL. Hartgerink JD. Donners JJJM. Stupp SI. J. Am. Chem. Soc. 2003, 125: 7146

Crossref Google Scholar
3b Bull SR. Guler MO. Bras RE. Venkatasubramanian PN. Stupp SI. Meade TJ. Bioconjugate Chem. 2005, 16: 1343

Crossref Google Scholar
3c Behanna HA. Donners JJJM. Gordon AC. Stupp SI. J. Am. Chem. Soc. 2005, 127: 1193

Crossref Google Scholar
3d Guler MO. Soukasene S. Hulvat JF. Stupp SI. Nano Lett. 2005, 5: 249

Crossref Google Scholar
4a Parsons JF. Xiao G. Gilliland GL. Armstrong RN. Biochemistry 1998, 37: 6286

Crossref Google Scholar
4b Pojitkov AE. Efremenko EN. Varfolomeev SD. J. Mol. Catal. B: Enzym. 2000, 10: 47

Crossref Google Scholar
5 Tahir H. Hindsgaul O. J. Org. Chem. 2000, 65: 911

Crossref Google Scholar
6a Effenberger F. Syed J. Tetrahedron: Asymmetry 1998, 9: 817

Article in Thieme Connect Google Scholar
6b Shenoy G. Kim P. Goodwin M. Nguyen Q.-A. Barry CE. Dowd CS. Heterocycles 2004, 63: 519

Article in Thieme Connect Google Scholar
6c Rajaram AR. Pu L. Org. Lett. 2006, 8: 2019

Article in Thieme Connect Google Scholar
6d Zografos AI. Georgiadis D. Synthesis 2006, 3157

Article in Thieme Connect Google Scholar
7a Gao WY. Agbaria R. Driscoll JS. Mitsuya H. J. Biol. Chem. 1994, 269: 12633

Crossref Google Scholar
7b Meier C. Synlett 1998, 233

Crossref Google Scholar
7c Saboulard D. Naesens L. Cahard D. Salgado A. Pathirana R. Velazquez S. McGuigan C. De Clercq E. Balzarini J. Mol. Pharmacol. 1999, 56: 693

Crossref Google Scholar
7d Bradshaw PC. Li J. Samuels DC. Biochem. J. 2005, 392: 363

Crossref Google Scholar
8 Lichtenthaler FW. Cuny E. Sakanaka O. Angew. Chem. Int. Ed. 2005, 44: 4944

Crossref Google Scholar
9a Gunasekera SP. McCarthy PJ. Kelly-Borges M. J. Am. Chem. Soc. 1996, 118: 8759

Crossref Google Scholar
9b Corey EJ. Roberts BE. J. Am. Chem. Soc. 1997, 119: 12425

Crossref Google Scholar
9c Takahashi M. Dodo K. Sugimoto Y. Aoyagi Y. Yamada Y. Hasimoto Y. Shirai R. Bioorg. Med. Chem. Lett. 2000, 10: 2571

Crossref Google Scholar
9d Miyaoka H. Kajiwara Y. Hara Y. Yamada Y. J. Org. Chem. 2001, 66: 1429

Crossref Google Scholar
9e Brohm D. Philippe N. Metzger S. Bhargava A. Muller O. Lieb F. Waldmann H. J. Am. Chem. Soc. 2002, 124: 13171

Crossref Google Scholar
10a Soriente A. Crispino A. De Rosa M. De Rosa S. Scettri A. Scognamiglio G. Villano R. Sodano G. Eur. J. Org. Chem. 2000, 943

Crossref Google Scholar
10b Basabe P. Delgado S. Marcos IS. Diez D. Diego A. De Roman M. Urones JG. J. Org. Chem. 2005, 70: 9480

Crossref Google Scholar
11a Mangnus EM. Stommen PLA. Zwanenburg B. J. Plant Growth Regul. 1992, 11: 91

Crossref Google Scholar
11b Kuad P. Borkovec M. Murr MD.-E. Le Gall T. Mioskowski Ch. Spiess B. J. Am. Chem. Soc. 2005, 127: 1323

Crossref Google Scholar
12a Mangnus EM. Zwanenburg B. J. Agric. Food Chem. 1992, 40: 1066

Crossref Google Scholar
12b Thuring JWJF. van Gaal AAMA. Hornes SJ. de Kok MM. Nefkens GHL. Zwanenburg B. J. Chem. Soc., Perkin Trans. 1 1997, 767

Crossref Google Scholar
13 Mal’kina AG. Shemyakina OA. Nosyreva VV. Albanov AI. Klyba LV. Zhanchipova ER. Trofimov BA. Mendeleev Commun. 2006, 228

Crossref Google Scholar
14 Mal’kina AG. Shemyakina OA. Nosyreva VV. Albanov AI. Klyba LV. Zhanchipova ER. Trofimov BA. Synthesis 2006, 637

Article in Thieme Connect Google Scholar
16 Batsanov SS. Russ. J. Inorg. Chem. (Engl. Transl.) 1991, 36: 1694

Google Scholar
17 Zefirov YuV. Crystallogr. Rep. 1999, 44: 1021

Google Scholar
18 Sheldrick GM. SHELXS-97 Program for Crystal Structure Determination University of Göttingen; Germany: 1997.

Google Scholar
19 Sheldrick GM. SHELXL-97 Program for the Refinement of Crystal Structures University of Göttingen; Germany: 1997.

Google Scholar
20a Landor SR. Demetriou B. Grzeskowiak R. Pavey D. J. Organomet. Chem. 1975, 93: 129

Article in Thieme Connect Google Scholar
20b Trofimov BA. Andriyankova LV. Shaikhudinova SI. Kazantseva TI. Mal’kina AG. Zhivet’ev SA. Afonin AV. Synthesis 2002, 853

Article in Thieme Connect Google Scholar

15

Crystallographic data: monoclinic, space group C2/c, a = 20.712(4) Å, b = 9.194(2) Å, c = 10.712(2) Å, β = 120.52(3)°, V = 1757.2(6) Å³, Z = 8, D_calcd = 1.39 g/cm³, reflections with [F ₀ > 4σ(F ₀)] = 1498, parameters refined = 167, R = 0.031. CCDC 628146 (for 11) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif