Asymmetric Synthesis of Tailor-Made Amino Acids Using Chiral Ni(II) Complexes of Schiff Bases. An Update of the Recent Literature

Overview

Journal Molecules

Publisher MDPI

Specialty Biology

Date 2020 Jun 18

PMID 32545684

Citations 3

Authors

Yupiao Zou

Jianlin Han

Ashot S Saghyan

Anna F Mkrtchyan

Hiroyuki Konno

Hiroki Moriwaki

Kunisuke Izawa

Vadim A Soloshonok

Affiliations

Soon will be listed here.

Abstract

Tailor-made amino acids are indispensable structural components of modern medicinal chemistry and drug design. Consequently, stereo-controlled preparation of amino acids is the area of high research activity. Over last decade, application of Ni(II) complexes of Schiff bases derived from glycine and chiral tridentate ligands has emerged as a leading methodology for the synthesis of various structural types of amino acids. This review article summarizes examples of asymmetric synthesis of tailor-made α-amino acids via the corresponding Ni(II) complexes, reported in the literature over the last four years. A general overview of this methodology is provided, with the emphasis given to practicality, scalability, cost-structure and recyclability of the chiral tridentate ligands.

Citing Articles

A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)-Schiff base complexes.

Dmitrieva A, Levitskiy O, Grishin Y, Magdesieva T Beilstein J Org Chem. 2023; 19:566-574.

PMID: 37153644 PMC: 10155621. DOI: 10.3762/bjoc.19.41.

Trapoxin A Analogue as a Selective Nanomolar Inhibitor of HDAC11.

Ho T, Peng C, Seto E, Lin H ACS Chem Biol. 2023; 18(4):803-809.

PMID: 36977486 PMC: 10127203. DOI: 10.1021/acschembio.2c00840.

Overview on Multienzymatic Cascades for the Production of Non-canonical α-Amino Acids.

Martinez-Rodriguez S, Torres J, Sanchez P, Ortega E Front Bioeng Biotechnol. 2020; 8:887.

PMID: 32850740 PMC: 7431475. DOI: 10.3389/fbioe.2020.00887.

References

Takeda R, Kawamura A, Kawashima A, Sato T, Moriwaki H, Izawa K . Second-order asymmetric transformation and its application for the practical synthesis of α-amino acids. Org Biomol Chem. 2018; 16(27):4968-4972. DOI: 10.1039/c8ob00963e. View

Craik D, Fairlie D, Liras S, Price D . The future of peptide-based drugs. Chem Biol Drug Des. 2012; 81(1):136-47. DOI: 10.1111/cbdd.12055. View

Wang J, Ji X, Shi J, Sun H, Jiang H, Liu H . Diastereoselective Michael reaction of chiral nickel(II) glycinate with nitroalkenes for asymmetric synthesis of β-substituted α,γ-diaminobutyric acid derivatives in water. Amino Acids. 2011; 42(5):1685-94. DOI: 10.1007/s00726-011-0870-x. View

Ellis T, Hochla V, Soloshonok V . Efficient synthesis of 2-aminoindane-2-carboxylic acid via dialkylation of nucleophilic glycine equivalent. J Org Chem. 2003; 68(12):4973-6. DOI: 10.1021/jo030065v. View

Periasamy M, Gurubrahamam R, Sanjeevakumar N, Dalai M, Alakonda L, Reddy P . Convenient methods for the synthesis of chiral amino alcohols and amines. Chimia (Aarau). 2013; 67(1-2):23-9. DOI: 10.2533/chimia.2013.23. View

Nian Y, Wang J, Moriwaki H, Soloshonok V, Liu H . Analysis of crystallographic structures of Ni(ii) complexes of α-amino acid Schiff bases: elucidation of the substituent effect on stereochemical preferences. Dalton Trans. 2017; 46(13):4191-4198. DOI: 10.1039/c7dt00014f. View

Han J, Jean M, Roussel C, Moriwaki H, Soloshonok V . Chromatographic approach to study the configurational stability of Ni(II) complexes of amino-acid Schiff bases possessing stereogenic nitrogen. Chirality. 2019; 31(4):328-335. DOI: 10.1002/chir.23059. View

Jackel C, Seufert W, Thust S, Koksch B . Evaluation of the molecular interactions of fluorinated amino acids with native polypeptides. Chembiochem. 2004; 5(5):717-20. DOI: 10.1002/cbic.200300840. View

Yamada T, Okada T, Sakaguchi K, Ohfune Y, Ueki H, Soloshonok V . Efficient asymmetric synthesis of novel 4-substituted and configurationally stable analogues of thalidomide. Org Lett. 2006; 8(24):5625-8. DOI: 10.1021/ol0623668. View

10.

Risgaard R, Nielsen S, Hansen K, Jensen C, Nielsen B, Traynelis S . Development of 2'-substituted (2S,1'R,2'S)-2-(carboxycyclopropyl)glycine analogues as potent N-methyl-d-aspartic acid receptor agonists. J Med Chem. 2013; 56(10):4071-81. PMC: 3689883. DOI: 10.1021/jm400346a. View

11.

Stevenazzi A, Marchini M, Sandrone G, Vergani B, Lattanzio M . Amino acidic scaffolds bearing unnatural side chains: an old idea generates new and versatile tools for the life sciences. Bioorg Med Chem Lett. 2014; 24(23):5349-56. DOI: 10.1016/j.bmcl.2014.10.016. View

12.

Hartman M, Josephson K, Szostak J . Enzymatic aminoacylation of tRNA with unnatural amino acids. Proc Natl Acad Sci U S A. 2006; 103(12):4356-61. PMC: 1450175. DOI: 10.1073/pnas.0509219103. View

13.

Levitskiy O, Grishin Y, Semivrazhskaya O, Ambartsumyan A, Kochetkov K, Magdesieva T . Individual ( A)- and ( C)-Fullerene-Based Nickel(II) Glycinates: Protected Chiral Amino Acids Directly Linked to a Chiral π-Electron System. Angew Chem Int Ed Engl. 2017; 56(10):2704-2708. DOI: 10.1002/anie.201609792. View

14.

Sorochinsky A, Acena J, Moriwaki H, Sato T, Soloshonok V . Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 2: aldol, Mannich addition reactions, deracemization and (S) to (R) interconversion of α-amino acids. Amino Acids. 2013; 45(5):1017-33. DOI: 10.1007/s00726-013-1580-3. View

15.

Graham D, Ashton W, BARASH L, Brown J, Brown R, Canning L . Inhibition of the mammalian beta-lactamase renal dipeptidase (dehydropeptidase-I) by (Z)-2-(acylamino)-3-substituted-propenoic acids. J Med Chem. 1987; 30(6):1074-90. DOI: 10.1021/jm00389a018. View

16.

Soloshonok V, Tang X, Hruby V, Van Meervelt L . Asymmetric synthesis of alpha,beta-dialkyl-alpha-phenylalanines via direct alkylation of a chiral alanine derivative with racemic alpha-alkylbenzyl bromides. A case of high enantiomer differentiation at room temperature. Org Lett. 2001; 3(3):341-3. DOI: 10.1021/ol000330o. View

17.

Acena J, Sorochinsky A, Soloshonok V . Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations. Amino Acids. 2014; 46(9):2047-73. DOI: 10.1007/s00726-014-1764-5. View

18.

Ojima I, Jameison F, Pete B, Radunz H, Schittenhelm C, Lindner H . Design, synthesis and enzyme inhibitory activities of new trifluoromethyl-containing inhibitors for angiotensin converting enzyme. Drug Des Discov. 1994; 11(2):91-113. View

19.

Han J, Romoff T, Moriwaki H, Konno H, Soloshonok V . Development of Hamari Ligands for Practical Asymmetric Synthesis of Tailor-Made Amino Acids. ACS Omega. 2019; 4(21):18942-18947. PMC: 6868592. DOI: 10.1021/acsomega.9b02940. View

20.

Mei H, Han J, Klika K, Izawa K, Sato T, Meanwell N . Applications of fluorine-containing amino acids for drug design. Eur J Med Chem. 2019; 186:111826. DOI: 10.1016/j.ejmech.2019.111826. View