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DOI: 10.1055/s-2007-983819
Synthesis of New Amino Acids with a 5-Imino-2,5-dihydro-3-furanyl Substituent at the Amino Group
Publikationsverlauf
Publikationsdatum:
30. Juli 2007 (online)
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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
-
1a
Mashkovskii MD. Drugs (In Russian) Novaya Volna; Moscow: 2003. -
1b
Kretschmer BD.Schmidt WJ.Kostrzewa RM.Herrera-Marschitz M. Amino Acids 2002, 23: 1 -
2a
Jsselstijn MI.Kaiser J.van Delft FL.Schoemaker HE.Rutjes FPJT. Amino Acids 2003, 24: 263 -
2b
Burger EC.Tunge JA. J. Am. Chem. Soc. 2006, 128: 10002 -
2c
Fülöp F.Martinek TA.Tóth GK. Chem. Soc. Rev. 2006, 35: 323 -
2d
Che Y.Marshall GR. J. Med. Chem. 2006, 49: 111 -
2e
Barsby T.Warabi K.Sørensen D.Zimmerman WT.Kelly MT.Andersen RJ. J. Org. Chem. 2006, 71: 6031 -
2f
Pollini GP.Benetti S.De Risi C.Zanirato V. Chem. Rev. 2006, 106: 2434 -
3a
Niece KL.Hartgerink JD.Donners JJJM.Stupp SI. J. Am. Chem. Soc. 2003, 125: 7146 -
3b
Bull SR.Guler MO.Bras RE.Venkatasubramanian PN.Stupp SI.Meade TJ. Bioconjugate Chem. 2005, 16: 1343 -
3c
Behanna HA.Donners JJJM.Gordon AC.Stupp SI. J. Am. Chem. Soc. 2005, 127: 1193 -
3d
Guler MO.Soukasene S.Hulvat JF.Stupp SI. Nano Lett. 2005, 5: 249 -
4a
Parsons JF.Xiao G.Gilliland GL.Armstrong RN. Biochemistry 1998, 37: 6286 -
4b
Pojitkov AE.Efremenko EN.Varfolomeev SD. J. Mol. Catal. B: Enzym. 2000, 10: 47 - 5
Tahir H.Hindsgaul O. J. Org. Chem. 2000, 65: 911 -
6a
Effenberger F.Syed J. Tetrahedron: Asymmetry 1998, 9: 817 -
6b
Shenoy G.Kim P.Goodwin M.Nguyen Q.-A.Barry CE.Dowd CS. Heterocycles 2004, 63: 519 -
6c
Rajaram AR.Pu L. Org. Lett. 2006, 8: 2019 -
6d
Zografos AI.Georgiadis D. Synthesis 2006, 3157 -
7a
Gao WY.Agbaria R.Driscoll JS.Mitsuya H. J. Biol. Chem. 1994, 269: 12633 -
7b
Meier C. Synlett 1998, 233 -
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 -
7d
Bradshaw PC.Li J.Samuels DC. Biochem. J. 2005, 392: 363 - 8
Lichtenthaler FW.Cuny E.Sakanaka O. Angew. Chem. Int. Ed. 2005, 44: 4944 -
9a
Gunasekera SP.McCarthy PJ.Kelly-Borges M. J. Am. Chem. Soc. 1996, 118: 8759 -
9b
Corey EJ.Roberts BE. J. Am. Chem. Soc. 1997, 119: 12425 -
9c
Takahashi M.Dodo K.Sugimoto Y.Aoyagi Y.Yamada Y.Hasimoto Y.Shirai R. Bioorg. Med. Chem. Lett. 2000, 10: 2571 -
9d
Miyaoka H.Kajiwara Y.Hara Y.Yamada Y. J. Org. Chem. 2001, 66: 1429 -
9e
Brohm D.Philippe N.Metzger S.Bhargava A.Muller O.Lieb F.Waldmann H. J. Am. Chem. Soc. 2002, 124: 13171 -
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 -
10b
Basabe P.Delgado S.Marcos IS.Diez D.Diego A.De Roman M.Urones JG. J. Org. Chem. 2005, 70: 9480 -
11a
Mangnus EM.Stommen PLA.Zwanenburg B. J. Plant Growth Regul. 1992, 11: 91 -
11b
Kuad P.Borkovec M.Murr MD.-E.Le Gall T.Mioskowski Ch.Spiess B. J. Am. Chem. Soc. 2005, 127: 1323 -
12a
Mangnus EM.Zwanenburg B. J. Agric. Food Chem. 1992, 40: 1066 -
12b
Thuring JWJF.van Gaal AAMA.Hornes SJ.de Kok MM.Nefkens GHL.Zwanenburg B. J. Chem. Soc., Perkin Trans. 1 1997, 767 - 13
Mal’kina AG.Shemyakina OA.Nosyreva VV.Albanov AI.Klyba LV.Zhanchipova ER.Trofimov BA. Mendeleev Commun. 2006, 228 - 14
Mal’kina AG.Shemyakina OA.Nosyreva VV.Albanov AI.Klyba LV.Zhanchipova ER.Trofimov BA. Synthesis 2006, 637 - 16
Batsanov SS. Russ. J. Inorg. Chem. (Engl. Transl.) 1991, 36: 1694 - 17
Zefirov YuV. Crystallogr. Rep. 1999, 44: 1021 - 18
Sheldrick GM. SHELXS-97 Program for Crystal Structure Determination University of Göttingen; Germany: 1997. - 19
Sheldrick GM. SHELXL-97 Program for the Refinement of Crystal Structures University of Göttingen; Germany: 1997. -
20a
Landor SR.Demetriou B.Grzeskowiak R.Pavey D. J. Organomet. Chem. 1975, 93: 129 -
20b
Trofimov BA.Andriyankova LV.Shaikhudinova SI.Kazantseva TI.Mal’kina AG.Zhivet’ev SA.Afonin AV. Synthesis 2002, 853
References
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, Dcalcd = 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