Home / Publications / Stereoselective arylthiolation of dehydroalanine in the NiII coordination environment: the stereoinductor of choice

Stereoselective arylthiolation of dehydroalanine in the NiII coordination environment: the stereoinductor of choice

Oleg Alexandrovich Levitskiy 1
Oleg Alexandrovich Levitskiy
, 
Olga Il'inichna Aglamazova 1
Olga Il'inichna Aglamazova
, 
Alena V Dmitrieva 1
Alena V Dmitrieva
, 
Vadim A Soloshonok 2, 3
Vadim A Soloshonok
, 
Hiroki Moriwaki 4
Hiroki Moriwaki
,  , 
Tatyana Vladimirovna Magdesieva 1
Tatyana Vladimirovna Magdesieva
10.1016/j.mencom.2021.04.018
Published 2021-04-28
Communication , Volume 31, Issue 3, 337-340
9
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Levitskiy O. A. et al. Stereoselective arylthiolation of dehydroalanine in the NiII coordination environment: the stereoinductor of choice // Mendeleev Communications. 2021. Vol. 31. No. 3. pp. 337-340.
GOST all authors (up to 50) Copy
Levitskiy O. A., Aglamazova O. I., Dmitrieva A. V., Soloshonok V. A., Moriwaki H., Grishin Y. K., Magdesieva T. V. Stereoselective arylthiolation of dehydroalanine in the NiII coordination environment: the stereoinductor of choice // Mendeleev Communications. 2021. Vol. 31. No. 3. pp. 337-340.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2021.04.018
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.018
TI - Stereoselective arylthiolation of dehydroalanine in the NiII coordination environment: the stereoinductor of choice
T2 - Mendeleev Communications
AU - Levitskiy, Oleg Alexandrovich
AU - Aglamazova, Olga Il'inichna
AU - Dmitrieva, Alena V
AU - Soloshonok, Vadim A
AU - Moriwaki, Hiroki
AU - Grishin, Yuri Konstantinovich
AU - Magdesieva, Tatyana Vladimirovna
PY - 2021
DA - 2021/04/28
PB - Mendeleev Communications
SP - 337-340
IS - 3
VL - 31
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2021_Levitskiy,
author = {Oleg Alexandrovich Levitskiy and Olga Il'inichna Aglamazova and Alena V Dmitrieva and Vadim A Soloshonok and Hiroki Moriwaki and Yuri Konstantinovich Grishin and Tatyana Vladimirovna Magdesieva},
title = {Stereoselective arylthiolation of dehydroalanine in the NiII coordination environment: the stereoinductor of choice},
journal = {Mendeleev Communications},
year = {2021},
volume = {31},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.018},
number = {3},
pages = {337--340},
doi = {10.1016/j.mencom.2021.04.018}
}
MLA
Cite this
MLA Copy
Levitskiy, Oleg Alexandrovich, et al. “Stereoselective arylthiolation of dehydroalanine in the NiII coordination environment: the stereoinductor of choice.” Mendeleev Communications, vol. 31, no. 3, Apr. 2021, pp. 337-340. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2021.04.018.

Keywords

arylthiolation
chiral template
cysteine derivatives
Michael addition
nickel complexes
Schiff bases
stereoselective synthesis
sulfides

Abstract

Arylthiolation of new dehydroalanine NiII Schiff-base complex containing (S)-2-[N-(N′-2,3-dichlorobenzylprolyl)amino]-5-chlorobenzophenone auxiliary affords (S,R)-cysteine derivatives in high chemical yield (65–88%) and with excellent diastereoselectivity (de up to 91%), which significantly exceeds that for the commonly used analogue depriving of three chlorine atoms.

References

2.
On-Demand Detachment of Succinimides on Cysteine to Facilitate (Semi)Synthesis of Challenging Proteins
Vamisetti G.B., Satish G., Sulkshane P., Mann G., Glickman M.H., Brik A.
Journal of the American Chemical Society, 2020
6.
Viracept (Nelfinavir Mesylate, AG1343):  A Potent, Orally Bioavailable Inhibitor of HIV-1 Protease
Kaldor S.W., Kalish V.J., Davies J.F., Shetty B.V., Fritz J.E., Appelt K., Burgess J.A., Campanale K.M., Chirgadze N.Y., Clawson D.K., Dressman B.A., Hatch S.D., Khalil D.A., Kosa M.B., Lubbehusen P.P., et. al.
Journal of Medicinal Chemistry, 1997
8.
S-Arylcysteine−Keratin Adducts as Biomarkers of Human Dermal Exposure to Aromatic Hydrocarbons
Kang-Sickel J.C., Fox D.D., Nam T., Jayaraj K., Ball L.M., French J.E., Klapper D.G., Gold A., Nylander-French L.A.
Chemical Research in Toxicology, 2008
11.
10.1016/j.mencom.2021.04.018_bib0055
Inoue
Mediators Inflammation, 2009
12.
General method of diastereo- and enantioselective synthesis of β-hydroxy-α-amino acids by condensation of aldehydes and ketones with glycine
Belokon Y.N., Bulychev A.G., Vitt S.V., Struchkov Y.T., Batsanov A.S., Timofeeva T.V., Tsyryapkin V.A., Ryzhov M.G., Lysova L.A.
Journal of the American Chemical Society, 1985
15.
Chemical Kinetic Resolution of Unprotected β-Substituted β-Amino Acids Using Recyclable Chiral Ligands
Zhou S., Wang J., Chen X., Aceña J.L., Soloshonok V.A., Liu H.
Angewandte Chemie - International Edition, 2014
16.
Recent approaches for asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes
Wang Y., Song X., Wang J., Moriwaki H., Soloshonok V.A., Liu H.
Amino Acids, 2017
17.
Asymmetric Synthesis of Tailor-Made Amino Acids Using Chiral Ni(II) Complexes of Schiff Bases. An Update of the Recent Literature
Zou Y., Han J., Saghyan A.S., Mkrtchyan A.F., Konno H., Moriwaki H., Izawa K., Soloshonok V.A.
Molecules, 2020
18.
Asymmetric synthesis of β-substituted α-amino acids via a chiral nlii complex of dehydroalanine
Belokon' Y.N., Sagyan A.S., Djamgaryan S.M., Bakhmutov V.I., Belikov V.M.
Tetrahedron, 1988
19.
Asymmetric synthesis ofS-alkyl-substituted (R)-cysteinesvia a chiral NiII complex of the Schiff's base of dehydroalanine with (S)-2-N-(N-benzylprolyl)aminobenzophenone
Saghiyan A.S., Geolchanyan A.V., Djamgaryan S.M., Vardapetyan S.M., Tararov V.I., Kuz'mina N.A., Ikonnikov N.S., Belokon Y.N., North M.
Russian Chemical Bulletin, 2000
20.
Asymmetric synthesis of (R)-S-(1,2,4-triazol-3-yl)cysteines by nucleophilic addition of triazolethiols to a NiIIcomplex with a chiral dehydroalanine Schiff base
Saghiyan A.S., Geolchanyan A.V., Manasyan L.L., Mkrtchyan G.M., Martirosyan N.R., Dadayan S.A., Kochickyan T.V., Harutyunyan V.S., Avetisyan A.A., Tararov V.I., Maleev V.I., Belokon" Y.N.
Russian Chemical Bulletin, 2004
21.
Operationally Convenient and Scalable Asymmetric Synthesis of (2S)- and (2R)-α-(Methyl)cysteine Derivatives through Alkylation of Chiral Alanine Schiff Base NiIIComplexes
Yamamoto J., Kawashima A., Kawamura A., Abe H., Moriwaki H., Shibata N., Soloshonok V.A.
European Journal of Organic Chemistry, 2017
22.
S-Michael Additions to Chiral Dehydroalanines as an Entry to Glycosylated Cysteines and a Sulfa-Tn Antigen Mimic
Aydillo C., Compañón I., Avenoza A., Busto J.H., Corzana F., Peregrina J.M., Zurbano M.M.
Journal of the American Chemical Society, 2014
23.
Bifunctional Chiral Dehydroalanines for Peptide Coupling and Stereoselective S-Michael Addition
Gutiérrez-Jiménez M.I., Aydillo C., Navo C.D., Avenoza A., Corzana F., Jiménez-Osés G., Zurbano M.M., Busto J.H., Peregrina J.M.
Organic Letters, 2016
25.
THE REACTION OF IODONIUM SALTS WITH THIOL COMPOUNDS
Sandin R.B., Christiansen R.G., Brown R.K., Kirkwood S.
Journal of the American Chemical Society, 1947
26.
General method for the asymmetric synthesis of α-amino acids via alkylation of the chiral nickel(II) Schiff base complexes of glycine and alanine
Belokon Y.N., Bakhmutov V.I., Chernoglazova N.I., Kochetkov K.A., Vitt S.V., Garbalinskaya N.S., Belikov V.M.
Journal of the Chemical Society Perkin Transactions 1, 1988
27.
10.1016/j.mencom.2021.04.018_bib0135
Organic Electrochemistry, 2015
28.
Electrochemically deprotonated chiral nickel(II) glycinate in stereoselective nucleophilic addition to michael acceptors: Advantages and limitations
Magdesieva T.V., Levitskiy O.A., Grishin Y.K., Ambartsumyan A.A., Kiskin M.A., Churakov A.V., Babievsky K.K., Kochetkov K.A.
Organometallics, 2014
29.
Stereoselective electrochemical thioalkylation of glycine in Ni(II) coordination environment
Levitskiy O.A., Grishin Y.K., Paseshnichenko K.A., Kochetkov K.A., Magdesieva T.V.
Tetrahedron Letters, 2018
30.
Chiral Nickel(II) Binuclear Complexes: Targeted Diastereoselective Electrosynthesis
Magdesieva T.V., Levitskiy O.A., Grishin Y.K., Ambartsumyan A.A., Paseshnichenko K.A., Kolotyrkina N.G., Kochetkov K.A.
Organometallics, 2014
31.
Individual (f,t A)- and (f,t C)-Fullerene-Based Nickel(II) Glycinates: Protected Chiral Amino Acids Directly Linked to a Chiral π-Electron System
Levitskiy O.A., Grishin Y.K., Semivrazhskaya O.O., Ambartsumyan A.A., Kochetkov K.A., Magdesieva T.V.
Angewandte Chemie - International Edition, 2017
32.
Which Stereoinductor Is Better for Asymmetric Functionalization of α‐Amino Acids in a Nickel(II) Coordination Environment? Experimental and DFT Considerations
Levitskiy O.A., Aglamazova O.I., Soloshonok V.A., Moriwaki H., Magdesieva T.V.
Chemistry - A European Journal, 2020
33.
Recyclable Ligands for the Non‐Enzymatic Dynamic Kinetic Resolution of Challenging α‐Amino Acids
Nian Y., Wang J., Zhou S., Wang S., Moriwaki H., Kawashima A., Soloshonok V.A., Liu H.
Angewandte Chemie - International Edition, 2015
34.
Preparative Method for Asymmetric Synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic Acid
Han J., Takeda R., Liu X., Konno H., Abe H., Hiramatsu T., Moriwaki H., Soloshonok V.A.
Molecules, 2019
35.
Stereoselective Electrosynthesis of β-Hydroxy-α-Amino Acids in the Form of NiII -Schiff-Base Complexes
Levitskiy O.A., Grishin Y.K., Magdesieva T.V.
European Journal of Organic Chemistry, 2019
36.
ACETYLATION IN VIVO OF p-BROMOPHENYL-d-CYSTEINE
du Vigneaud V., Wood J.L., Binkley F.
Journal of Biological Chemistry, 1941
37.
Cell-Penetrating Peptides Containing Fluorescent d -Cysteines
Navo C.D., Asín A., Gómez-Orte E., Gutiérrez-Jiménez M.I., Compañón I., Ezcurra B., Avenoza A., Busto J.H., Corzana F., Zurbano M.M., Jiménez-Osés G., Cabello J., Peregrina J.M.
Chemistry - A European Journal, 2018