Home / Publications / Chemoenzymatic arabinosylation of 2-aminopurines bearing the chiral fragment of 7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines

Chemoenzymatic arabinosylation of 2-aminopurines bearing the chiral fragment of 7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines

Barbara Zlatkovna Eletskaya 1
Barbara Zlatkovna Eletskaya
, 
Irina Dmitrievna Konstantinova 1
Irina Dmitrievna Konstantinova
, 
Alexander Sergeyevich Paramonov 1
Alexander Sergeyevich Paramonov
, 
Roman Stanislavovich Esipov 1
Roman Stanislavovich Esipov
, 
Dmitry Andreevich Gruzdev 2
Dmitry Andreevich Gruzdev
, 
Alexey Yur'evich Vigorov 2
Alexey Yur'evich Vigorov
, 
Galina L'vovna Levit 2
Galina L'vovna Levit
, 
Anatoly Ivanovich Miroshnikov 1
Anatoly Ivanovich Miroshnikov
, 
Victor Pavlovich Krasnov 2
Victor Pavlovich Krasnov
, 
10.1016/j.mencom.2016.01.003
Published 2015-12-30
Communication , Volume 26, Issue 1, 6-8
8
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Eletskaya B. Z. et al. Chemoenzymatic arabinosylation of 2-aminopurines bearing the chiral fragment of 7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines // Mendeleev Communications. 2015. Vol. 26. No. 1. pp. 6-8.
GOST all authors (up to 50) Copy
Eletskaya B. Z., Konstantinova I. D., Paramonov A. S., Esipov R. S., Gruzdev D. A., Vigorov A. Y., Levit G. L., Miroshnikov A. I., Krasnov V. P., Charushin V. N. Chemoenzymatic arabinosylation of 2-aminopurines bearing the chiral fragment of 7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines // Mendeleev Communications. 2015. Vol. 26. No. 1. pp. 6-8.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2016.01.003
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.01.003
TI - Chemoenzymatic arabinosylation of 2-aminopurines bearing the chiral fragment of 7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines
T2 - Mendeleev Communications
AU - Eletskaya, Barbara Zlatkovna
AU - Konstantinova, Irina Dmitrievna
AU - Paramonov, Alexander Sergeyevich
AU - Esipov, Roman Stanislavovich
AU - Gruzdev, Dmitry Andreevich
AU - Vigorov, Alexey Yur'evich
AU - Levit, Galina L'vovna
AU - Miroshnikov, Anatoly Ivanovich
AU - Krasnov, Victor Pavlovich
AU - Charushin, Valery Nikolaevich
PY - 2015
DA - 2015/12/30
PB - Mendeleev Communications
SP - 6-8
IS - 1
VL - 26
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2015_Eletskaya,
author = {Barbara Zlatkovna Eletskaya and Irina Dmitrievna Konstantinova and Alexander Sergeyevich Paramonov and Roman Stanislavovich Esipov and Dmitry Andreevich Gruzdev and Alexey Yur'evich Vigorov and Galina L'vovna Levit and Anatoly Ivanovich Miroshnikov and Victor Pavlovich Krasnov and Valery Nikolaevich Charushin},
title = {Chemoenzymatic arabinosylation of 2-aminopurines bearing the chiral fragment of 7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines},
journal = {Mendeleev Communications},
year = {2015},
volume = {26},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.01.003},
number = {1},
pages = {6--8},
doi = {10.1016/j.mencom.2016.01.003}
}
MLA
Cite this
MLA Copy
Eletskaya, Barbara Zlatkovna, et al. “Chemoenzymatic arabinosylation of 2-aminopurines bearing the chiral fragment of 7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines.” Mendeleev Communications, vol. 26, no. 1, Dec. 2015, pp. 6-8. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2016.01.003.

Abstract

Chemoenzymatic transglycosylation of 2-aminopurine conjugates with enantiomerically pure 7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazines under the action of recombinant E. coli purine nucleoside phosphorylase afforded the corresponding arabinofuranosides, yields of the target compounds being dependent on both the structure and configuration of the fragment of heterocyclic amine attached at C-6 position of purine moiety.

References

1.
N6-substituted C5′-modified adenosines as A1 adenosine receptor agonists
Ashton T.D., Baker S.P., Hutchinson S.A., Scammells P.J.
Bioorganic and Medicinal Chemistry, 2008
2.
Synthesis and evaluation of new N6-substituted adenosine-5′-N-methylcarboxamides as A3 adenosine receptor agonists
Devine S.M., Gregg A., Figler H., McIntosh K., Urmaliya V., Linden J., Pouton C.W., White P.J., Bottle S.E., Scammells P.J.
Bioorganic and Medicinal Chemistry, 2010
3.
Hybrid Ortho/Allosteric Ligands for the Adenosine A1 Receptor
Narlawar R., Lane J.R., Doddareddy M., Lin J., Brussee J., IJzerman A.P.
Journal of Medicinal Chemistry, 2010
4.
Structure–Activity Relationships of Truncated C2- or C8-Substituted Adenosine Derivatives as Dual Acting A2A and A3 Adenosine Receptor Ligands
Hou X., Majik M.S., Kim K., Pyee Y., Lee Y., Alexander V., Chung H., Lee H.W., Chandra G., Lee J.H., Park S., Choi W.J., Kim H.O., Phan K., Gao Z., et. al.
Journal of Medicinal Chemistry, 2011
5.
Fludarabine
Ross S.R., McTavish D., Faulds D.
Drugs, 1993
6.
Discovery and development of clofarabine: a nucleoside analogue for treating cancer
Bonate P.L., Arthaud L., Cantrell W.R., Stephenson K., Secrist J.A., Weitman S.
Nature Reviews Drug Discovery, 2006
7.
Adenosine Analogues as Inhibitors of Trypanosoma brucei Phosphoglycerate Kinase:  Elucidation of a Novel Binding Mode for a 2-Amino-N6-Substituted Adenosine
Bressi J.C., Choe J., Hough M.T., Buckner F.S., Van Voorhis W.C., Verlinde C.L., Hol W.G., Gelb M.H.
Journal of Medicinal Chemistry, 2000
10.
Synthesis of novel substituted purine derivatives and identification of the cell death mechanism
Demir Z., Guven E.B., Ozbey S., Kazak C., Atalay R.C., Tuncbilek M.
European Journal of Medicinal Chemistry, 2015
11.
F. B. Pallier and J. L. Haesslein, French Patent, 2851248, C07D, 2004.(Chem. Abstr., 2004, 141, 206968).
12.
G. Chen, T.D. Cushing, B. Fisher, X. He, K. Li, Z. Li, L.R. McGee, V. Pattaropong, P. Faulder, J.L. Seganish and Y. Shin, PCT Patent, WO 2009158011, C07D, 2009.(Chem. Abstr., 2009, 152, 119631).
13.
C. Guibourdenche, S. Hintermann, K. Hurth, S. Jacquier, C. Kalis, H. Moebitz and N. Soldermann, PCT Patent, WO 2014128612, C07D, 2014.(Chem. Abstr., 2014, 161, 433034).
15.
2,6,9-trisubstituted purines: optimization towards highly potent and selective CDK1 inhibitors.
Imbach P., Capraro H., Furet P., Mett H., Meyer T., Zimmermann J.
Bioorganic and Medicinal Chemistry Letters, 1999
16.
Holý A., Votruba I., Tloušťová E., Masojídková M.
Collection of Czechoslovak Chemical Communications, 2002
17.
An efficient synthesis of substituted cytosines and purines under focused microwave irradiation
Huang L., Cherng Y., Cheng Y., Jang J., Chao Y., Cherng Y.
Tetrahedron, 2007
19.
10.1016/j.mencom.2016.01.003_bib0095
Hu
J. Mex. Chem. Soc., 2010
20.
Vigorov A.Y., Krasnov V.P., Gruzdev D.A., Men'shikova A.A., Demin A.M., Levit G.L., Charushin V.N.
Mendeleev Communications, 2014
21.
Facilitation of addition–elimination reactions in pyrimidines and purines using trifluoroacetic acid in trifluoroethanol
Whitfield H.J., Griffin R.J., Hardcastle I.R., Henderson A., Meneyrol J., Mesguiche V., Sayle K.L., Golding B.T.
Chemical Communications, 2003
22.
Trifluoroacetic Acid in 2,2,2-Trifluoroethanol Facilitates SNAr Reactions of Heterocycles with Arylamines
Carbain B., Coxon C.R., Lebraud H., Elliott K.J., Matheson C.J., Meschini E., Roberts A.R., Turner D.M., Wong C., Cano C., Griffin R.J., Hardcastle I.R., Golding B.T.
Chemistry - A European Journal, 2014
23.
Krasnov V.P., Gruzdev D.A., Chulakov E.N., Vigorov A.Y., Musiyak V.V., Matveeva T.V., Tumashov A.A., Levit G.L., Charushin V.N.
Mendeleev Communications, 2015
24.
10.1016/j.mencom.2016.01.003_bib0125
Konstantinova
Synthesis, 2011
25.
The chemoenzymatic synthesis of clofarabine and related 2′-deoxyfluoroarabinosyl nucleosides: the electronic and stereochemical factors determining substrate recognition by E. coli nucleoside phosphorylases
Fateev I.V., Antonov K.V., Konstantinova I.D., Muravyova T.I., Seela F., Esipov R.S., Miroshnikov A.I., Mikhailopulo I.A.
Beilstein Journal of Organic Chemistry, 2014