Synthesis 2007(17): 2641-2646  
DOI: 10.1055/s-2007-983819
PAPER
© Georg Thieme Verlag Stuttgart · New York

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’kinaa, Olesya A. Shemyakinaa, Angela P. Borisovaa, Valentina V. Nosyrevaa, Oleg A. Dyachenkob, Olga N. Kazhevab, Gennadii G. Alexandrovc
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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Publikationsverlauf

Received 10 April 2007
Publikationsdatum:
30. Juli 2007 (online)

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.

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, 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