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Peptide-Catalysis in Asymmetric Organic Synthesis

  • Mehdi Mogharabi
  • Shahla Rezaei
  • Mohammad Ali Faramarzi

Trends in Peptide and Protein Sciences, Vol. 1 No. 3 (2017), 8 May 2017 , Page 88-98
https://doi.org/10.22037/tpps.v1i3.16317 Published: 2017-05-08

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Abstract

Stereo-selectivity is an important feature in the development of the synthesis of biologically active organic compounds. In this process, (bio) catalysts exhibit substrate specificity that allows high levels of chemo- and regio-selectivity. Over the past decade, several peptides have been developed as effective bio-catalysts for a range of synthetically valuable reactions. In comparison with proteins owing a large number of amino acids and high molecular weights, peptide-catalysts possess only a few amino acid residues, which may adopt a secondary structure suitable for synthesis of desired chiral products. In addition, the flexible nature of peptides consents for tuning of reactivity and selectivity by replacing amino acid residues. These unique aspects provide attractive biocatalysts platform for asymmetric syntheses.

Highlights

  • Asymmetric catalysis has an impressive progression in the manufacture of pharmaceuticals.
  • Enzymes and natural/synthetic peptides are attractive biocatalysts of the chiral reactions.
  • Peptides show unique features compared with other catalysts in asymmetric catalysis.

 

Keywords:
  • Peptide
  • Organic synthesis
  • Enzyme
  • Stereo-selectivity
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How to Cite

1.
Mogharabi M, Rezaei S, Faramarzi MA. Peptide-Catalysis in Asymmetric Organic Synthesis. Trends Pept. Protein Sci. [Internet]. 2017 May 8 [cited 2026 Jul. 28];1(3):88-9. Available from: https://journals.sbmu.ac.ir/protein/article/view/16317
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References

Akagawa, K., Iwasaki, Y. and K. Kudo, (2016) "Library screening in aqueous media to develop a highly active peptide catalyst for enantioselective Michael addition of a malonate." European Journal of Organic Chemistry, 2016 (26): 4460–4464.

Behrendt, R., White, P. and J. Offer, (2016) "Advances in Fmoc solid‐phase peptide synthesis." Journal of Peptide Science, 22 (1): 4–27.

Cakmak, Y., Erbas-Cakmak, S. and D. A. Leigh, (2016) "Asymmetric catalysis with a mechanically point-chiral rotaxane." Journal of the American Chemical Society, 138 (6): 1749–1751.

Chebil, L., Humeau, C., Falcimaigne, A., Engasser, J. M. and M. Ghoul, (2006). "Enzymatic acylation of flavonoids." Process Biochemistry, 41 (11): 2237–2251.

Das, S., Majumdar, N., De, C. K., Kundu, D. S., Döhring, A., Garczynski, A. and B. List, (2017) "Asymmetric catalysis of the carbonyl-amine condensation: kinetic resolution of primary amines." Journal of the American Chemical Society, 139: 1357-1359. DOI: 10.1021/jacs.6b12176.

Diener, M. E., Metrano, A. J., Kusano, S. and S. J. Miller, (2015) "Enantioselective synthesis of 3-arylquinazolin-4 (3 H)-ones via peptide-catalyzed atroposelective bromination." Journal of the American Chemical Society, 137 (38): 12369–12377.

Fischer, E. and E. Fourneau, (1901). "Ueber einige derivate des glykocolls." European Journal of Inorganic Chemistry, 34 (2): 2868–2877.

Formaggio, F., Bonchio, M., Crisma, M., Peggion, C., Mezzato, S., Polese, A., Barazza, A., Antonello, S., Maran, F., Broxterman, Q.B. and B. Kaptein, (2002) "Nitroxyl peptides as catalysts of enantioselective oxidations." Chemistry–A European Journal, 8 (1): 84–93.

Forootanfar, H., Faramarzi, M. A., Shahverdi, A. R. and M. T. Yazdi, (2011) "Purification and biochemical characterization of extracellular laccase from the ascomycete Paraconiothyrium variabile." Bioresource Technology, 102 (2): 1808–1814.

Grünenfelder, C. E., Kisunzu, J. K. and H. Wennemers, (2016) "Peptide‐catalyzed stereoselective conjugate addition reactions of aldehydes to maleimide." Angewandte Chemie International Edition, 55 (30): 8571–8574.

Gustafson, J. L., Lim, D. and S. J. Miller, (2010). "Dynamic kinetic resolution of biaryl atropisomers via peptide-catalyzed asymmetric bromination." Science, 328 (5983): 1251–1255.

Han, S. Y. and Y. A. Kim, (2004) "Recent development of peptide coupling reagents in organic synthesis." Tetrahedron, 60 (11): 2447–2467.

Han, S. and S. J. Miller, (2013) "Asymmetric catalysis at a distance: catalytic, site-selective phosphorylation of teicoplanin." Journal of the American Chemical Society, 135 (33): 12414–12421.

Horstmann, T. E., Guerin, D. J. and S. J. Miller, (2000). "Asymmetric Conjugate Addition of Azide to α, β‐Unsaturated Carbonyl Compounds Catalyzed by Simple Peptides." Angewandte Chemie, 112 (20): 3781–3784.

Itsuno, S., Sakakura, M. and K. Ito, (1990) "Polymer-supported poly (amino acids) as new asymmetric epoxidation catalyst of. alpha., beta-unsaturated ketones." The Journal of Organic Chemistry, 55 (24): 6047–6049.

Jakobsche, C. E., Peris, G. and S. J. Miller, (2008). "Functional Analysis of an Aspartate‐Based Epoxidation Catalyst with Amide‐to‐Alkene Peptidomimetic Catalyst Analogues." Angewandte Chemie International Edition, 47 (35): 6707–6711.

Juliá, S., Masana, J. and J. C. Vega, (1980) "Synthetic Enzymes”. Highly Stereoselective Epoxidation of Chalcone in a Triphasic Toluene‐Water‐Poly [(S)‐alanine] System." Angewandte Chemie International Edition in English, 19 (11): 929–931.

Kent, S. B. (2009) "Total chemical synthesis of proteins." Chemical Society Reviews, 38 (2): 338–351.

Lewis, C. A. and S. J. Miller, (2006) "Site‐selective derivatization and remodeling of erythromycin A by using simple peptide‐based chiral catalysts." Angewandte Chemie, 118 (34): 5744–5747.

Lewis, C. A., Gustafson, J. L., Chiu, A., Balsells, J., Pollard, D., Murry, J. and S. J. Miller, (2008). "A case of remote asymmetric induction in the peptide-catalyzed desymmetrization of a bis (phenol)." Journal of the American Chemical Society, 130 (48): 16358–16365.

Liao, R. Z., Santoro, S., Gotsev, M., Marcelli, T. and F. Himo, (2016) "Origins of stereoselectivity in peptide-catalyzed kinetic resolution of alcohols." ACS Catalysis, 6 (2): 1165–1171.

Mennen, S. M., Blank, J. T., Tran-Dubé, M. B., Imbriglio, J. E. and S. J. Miller, (2005). "A peptide-catalyzed asymmetric Stetter reaction." Chemical Communications, 2: 195–197.

Metrano, A. J. and S. J. Miller, (2014) "Peptide-catalyzed conversion of racemic oxazol-5 (4 H)-ones into enantiomerically enriched α-amino acid derivatives." The Journal of Organic Chemistry, 79 (4): 1542–1554.

Milbeo, P., Maurent, K., Moulat, L., Lebrun, A., Didierjean, C., Aubert, E., Martines, J. and M. Calmes, (2016). "N-Pyrrolidine-based α/β-peptides incorporating ABOC, a constrained bicyclic β-amino acid, for asymmetric aldol reaction catalysis." Tetrahedron, 72 (13): 1706–1715.

Miranda, L. P. and P. F. Alewood, (2000) "Challenges for protein chemical synthesis in the 21st century: bridging genomics and proteomics." Peptide Science, 55 (3): 217–226.

Mogharabi, M. and M. A. Faramarzi, (2014) "Laccase and laccase‐mediated systems in the synthesis of organic compounds." Advanced Synthesis & Catalysis, 356 (5): 897–927.

Matsumoto, Y., Matsumoto, Y., Inoue, J. and R. Ueoka, (1993) "Extraordinary diastereoselectivity coupled to altered structure of dipeptide esters." Chemistry Letters, 22 (8): 1303–1304.

Newton, C. G., Kossler, D. and N. Cramer, (2016) "Asymmetric catalysis powered by chiral cyclopentadienyl ligands." Journal of the American Chemical Society, 138 (12): 3935–3941.

Orellana‐Coca, C., Camocho, S., Adlercreutz, D., Mattiasson, B., and R. Hatti‐Kaul, (2005) "Chemo‐enzymatic epoxidation of linoleic acid: Parameters influencing the reaction." European Journal of Lipid Science and Technology, 107 (12): 864–870.

Palomo, J. M. (2014). "Solid-phase peptide synthesis: an overview focused on the preparation of biologically relevant peptides." RSC Advances, 4 (62): 32658–32672.

Pattabiraman, V. R. and J. W. Bode, (2011) "Rethinking amide bond synthesis." Nature, 480 (7378): 471–479.

Procházková, E., Kolmer, A., Ilgen, J., Schwab, M., Kaltschnee, L., Fredersdorf, M., Schmidts, V., Wende, R. C., Schreiner, P. R. and C. M. Thiele, (2016) "Uncovering key structural features of an enantioselective peptide‐catalyzed acylation utilizing advanced NMR techniques." Angewandte Chemie International Edition, 55 (51): 15754–15759.

Rezaei, S., Shahverdi, A. R. and M. A. Faramarzi, (2017) "Isolation, one-step affinity purification, and characterization of a polyextremotolerant laccase from the halophilic bacterium Aquisalibacillus elongatus and its application in the delignification of sugar beet pulp." Bioresource Technology, 230: 67–75.

Schwieter, K. E. and J. N. Johnston, (2016) "On-demand complex peptide synthesis: an aspirational (and Elusive) goal for peptide synthesis." Journal of the American Chemical Society, 138 (43): 14160–14169.

Tsogoeva, S. B. and S. B. Jagtap, (2004). "Dual catalyst control in the chiral diamine-dipeptide-catalyzed asymmetric Michael addition." Synlett, 2004 (14): 2624–2626.

Tsogoeva, S. B., Jagtap, S. B., Ardemasova, Z. A. and V. N. Kalikhevich, (2004). "Trends in asymmetric Michael reactions catalysed by tripeptides in combination with an achiral additive in different solvents." European Journal of Organic Chemistry, 2004 (19): 4014–4019.

Tsogoeva, S. B., Jagtap, S. B. and Z. A. Ardemasova, (2006). "4-trans-Amino-proline based di-and tetrapeptides as organic catalysts for asymmetric C–C bond formation reactions." Tetrahedron: Asymmetry, 17 (6): 989–992.

Ueda, A., Umeno, T., Doi, M., Akagawa, K., Kudo, K. and M. Tanaka, (2016) "Helical-Peptide-catalyzed enantioselective michael addition reactions and their mechanistic insights." The Journal of Organic Chemistry, 81 (15): 6343–6356.

Ueoka, R., Matsumoto, Y., Goto, K., Ito, T., Mori, S., Matsumoto, Y., Sakoguchi, A., Ihara, Y. and F. Hirata, (1996) "A remarkably enhanced diastereoselectivity for the hydrolysis of dipeptide esters responding to pH and temperature in buffer solutions." Tetrahedron Letters, 37 (20): 3461–3464.

Ueoka, R., Goto, K., Tanoue, O., Miki, A., Yoshimitsu, S., Imamura, C., Ihara, Y. and Y. Murakami, (1999) "Diastereoselective specificity for the hydrolysis of dipeptide esters in aqueous media." Chemistry Letters, 28 (1): 73–74.

Wachtmeister, J. and D. Rother, (2016) "Recent advances in whole cell biocatalysis techniques bridging from investigative to industrial scale." Current Opinion in Biotechnology, 42: 169–177.

Wiesner, M., Revell, J. D. and H. Wennemers, (2008). "Tripeptides as Efficient Asymmetric Catalysts for 1,4‐Addition Reactions of Aldehydes to Nitroolefins–A Rational Approach." Angewandte Chemie, 120 (10): 1897–1900.

Wennemers, H. (2011) "Asymmetric catalysis with peptides." Chemical Communications, 47 (44): 12036–12041.

Yuki, O., Zhang, Y., Ge, J. and Z. Liu, (2016) "Epoxidation of Fatty Acids by Pluronic-Conjugated Lipase in Organic Media." Catalysis Letters, 146 (6): 1073–1078.

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Journal Name:

Trends in Peptide and Protein Sciences (TPPS)

Journal Abbreviation:

Trends Pept. Protein Sci.

eISSN:

2538-2446

 

 

 

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