Chemo-, Regio- and Stereospecific Synthesis of Unnatural, Fluorescent Amino Acids by Condensation of L-Lysine and 1-Vinylpyrrole-2-carbaldehydes
Publication type: Journal Article
Publication date: 2010-07-16
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
A new family of unnatural, optically active amino acids containing the pyrrole moiety have been synthesized by condensation of 1‐vinylpyrrole‐2‐carbaldehydes with L‐lysine under mild conditions (EtOH, room temp., 2.5–3 h, 0.5 wt.‐% of CF3CO2H) in up to 90 % yields. Unlike non‐vinylated analogues, 1‐vinylpyrrole‐2‐carbaldehydes react chemo‐, regio‐ and stereospecifically with an ϵ‐amino group only to afford products of exclusively (E) configuration. The amino acids synthesized containing aromatic or condensed aromatic substitutents in the pyrrole ring fluoresce in the UV/Vis region (λmax = 350–382 nm, Stokes shifts 6150–7800 cm–1).
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Total citations:
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Citations from 2024:
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Ivanov A. V. et al. Chemo-, Regio- and Stereospecific Synthesis of Unnatural, Fluorescent Amino Acids by Condensation of L-Lysine and 1-Vinylpyrrole-2-carbaldehydes // European Journal of Organic Chemistry. 2010. Vol. 2010. No. 24. pp. 4554-4558.
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Ivanov A. V., Ushakov I. A., Petrushenko K. B., Mikhaleva A. I., Trofimov B. A. Chemo-, Regio- and Stereospecific Synthesis of Unnatural, Fluorescent Amino Acids by Condensation of L-Lysine and 1-Vinylpyrrole-2-carbaldehydes // European Journal of Organic Chemistry. 2010. Vol. 2010. No. 24. pp. 4554-4558.
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TY - JOUR
DO - 10.1002/ejoc.201000620
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201000620
TI - Chemo-, Regio- and Stereospecific Synthesis of Unnatural, Fluorescent Amino Acids by Condensation of L-Lysine and 1-Vinylpyrrole-2-carbaldehydes
T2 - European Journal of Organic Chemistry
AU - Ivanov, Andrey V
AU - Ushakov, Igor A.
AU - Petrushenko, Konstantin B.
AU - Mikhaleva, Al'bina I
AU - Trofimov, Boris A.
PY - 2010
DA - 2010/07/16
PB - Wiley
SP - 4554-4558
IS - 24
VL - 2010
SN - 1434-193X
SN - 1099-0690
ER -
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@article{2010_Ivanov,
author = {Andrey V Ivanov and Igor A. Ushakov and Konstantin B. Petrushenko and Al'bina I Mikhaleva and Boris A. Trofimov},
title = {Chemo-, Regio- and Stereospecific Synthesis of Unnatural, Fluorescent Amino Acids by Condensation of L-Lysine and 1-Vinylpyrrole-2-carbaldehydes},
journal = {European Journal of Organic Chemistry},
year = {2010},
volume = {2010},
publisher = {Wiley},
month = {jul},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201000620},
number = {24},
pages = {4554--4558},
doi = {10.1002/ejoc.201000620}
}
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MLA
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Ivanov, Andrey V., et al. “Chemo-, Regio- and Stereospecific Synthesis of Unnatural, Fluorescent Amino Acids by Condensation of L-Lysine and 1-Vinylpyrrole-2-carbaldehydes.” European Journal of Organic Chemistry, vol. 2010, no. 24, Jul. 2010, pp. 4554-4558. https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.201000620.
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