Recent advances in chemoenzymatic peptide syntheses

Molecules

Volumn 19, Issue 9, 2014, Pages 13755-13774

  Yazawa, Kenjiro ^a   Numata, Keiji ^a  

^a Elements Chemistry Laboratory   (Japan)

Author keywords

Chemoenzymatic; Enzyme; Enzyme engineering; Peptide; Protease; Reaction mechanisms; Reaction media; Substrate mimetics

Indexed keywords

IONIC LIQUID; PEPTIDE; PEPTIDE HYDROLASE; TRIACYLGLYCEROL LIPASE;

BIOCATALYSIS; CHEMISTRY; PH; PROTEIN ENGINEERING; SYNTHESIS; TEMPERATURE;

BIOCATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; HYDROGEN-ION CONCENTRATION; IONIC LIQUIDS; LIPASE; PEPTIDE HYDROLASES; PEPTIDES; PROTEIN ENGINEERING; TEMPERATURE;

EID: 84907104280     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules190913755     Document Type: Review

References (75)

1. Nuijens, T.; Quaedflieg, P.J.L.M.; Jakubke, H.D. Hydrolysis and synthesis of peptides. In Enzyme Catalysis in Organic Synthesis, 3rd ed.; Drauz, K., Gröger, H., May, O., Eds.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2012; pp. 675-748.
2. Merrifield, R.B. Solid-phase peptide synthesis. Adv. Enzymol. Relat. Areas Mol. Biol. 1969, 32, 221-296.
3. Löfblom, J. Bacterial display in combinatorial protein engineering. Biotechnol. J. 2011, 6, 1115-1129.
4. Baker, P.J.; Numata, K. Polymerization of peptide polymers for biomaterial applications. In Polymer Science; Yi{dotless}lmaz, F., Ed.; Intech: Rijeka, Croatia, 2013; pp. 229-246.
5. Bergmann, M.; Niemann, C. Newer biological aspects of protein chemistry. Science 1937, 86, 187-190.
6. Bergmann, M.; Fruton, J.S. Some synthetic and hydrolytic experiments with chymotrypsin. J. Biol. Chem. 1938, 124, 321-329.
7. Yu, H.; Chokhawala, H.A.; Huang, S.; Chen, X. One-pot three-enzyme chemoenzymatic approach to the synthesis of sialosides containing natural and non-natural functionalities. Nat. Protoc. 2006, 1, 2485-2492.
8. Guzmán, F.; Barberis, S.; Illanes, A. Peptide synthesis: Chemical or enzymatic. Electron. J. Biotechnol. 2007, 10, 279-314.
9. Schröder, H.; Strohmeier, G.A.; Leypold, M.; Nuijens, T.; Quaedflieg, P.J.L.M.; Breinbauer, R. Racemization-free chemoenzymatic peptide synthesis enabled by the ruthenium-catalyzed synthesis of peptide enol esters via alkyne-addition and subsequent conversion using alcalasecross-linked enzyme aggregates. Adv. Synth. Catal. 2013, 355, 1799-1807.
10. Cheng, H.N. Enzyme-catalyzed synthesis of polyamides and polypeptides. In Biocatalysis in Polymer Chemistry; Loos, K., Ed.; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2010; pp. 131-141.
11. Schechter, I.; Berger, A. On the size of the active site in proteases. I. Papain. Biochem. Biophys. Res. Commun. 1967, 27, 157-162.
12. Bordusa, F. Proteases in organic synthesis. Chem. Rev. 2002, 102, 4817-4867.
13. Chen, F.; Zhang, F.; Wang, A.; Li, H.; Wang, Q.; Zeng, Z.; Xie, T. Recent progress in the chemo-enzymatic peptide synthesis. Afr. J. Pharm. Pharmacol. 2010, 4, 721-730.
14. Yagasaki, M.; Hashimoto, S. Synthesis and application of dipeptides; current status and perspectives. Appl. Microbiol. Biotechnol. 2008, 81, 13-22.
15. Baker, P.J.; Numata, K. Chemoenzymatic synthesis of poly(L-alanine) in aqueous environment. Biomacromolecules. 2012, 13, 947-951.
16. Fukuoka, T.; Tachibana, Y.; Tonami, H.; Uyama, H.; Kobayashi, S. Enzymatic polymerization of tyrosine derivatives. Peroxidase- and protease-catalyzed synthesis of poly(tyrosine)s with different structures. Biomacromolecules 2002, 3, 768-774.
17. Uyama, H.; Fukuoka, T.; Komatsu, I.; Watanabe, T.; Kobayashi, S. Protease-catalyzed regioselective polymerization and copolymerization of glutamic acid diethyl ester. Biomacromolecules 2002, 3, 318-323.
18. Viswanathan, K.; Schofield, M.H.; Teraoka, I.; Gross, R.A. Surprising metal binding properties of phytochelatin-like peptides prepared by protease-catalysis. Green Chem. 2012, 14, 1020-1029.
19. Schwab, L.W.; Kloosterman, W.M.J.; Konieczny, J.; Loos, K. Papain catalyzed (co)oligomerization of α-amino acids. Polymers 2012, 4, 710-740.
20. Qin, X.; Khuong, A.C.; Yu, Z.; Du, W.; Decatur, J.; Gross, R.A. Simplifying alternating peptide synthesis by protease-catalyzed dipeptide oligomerization. Chem. Commun. 2013, 49, 385-387.
21. Baker, P.J.; Patwardhan, S.V.; Numata, K. Synthesis of homopolypeptides by aminolysis mediated by proteases encapsulated in silica nanospheres. Macromol. Biosci. 2014, in press.
22. Numata, K.; Baker, P.J. Synthesis of adhesive peptides similar to those found in blue mussel (Mytilus edulis) using papain and tyrosinase. Biomacromolecules 2014, 15, 3206-3212.
23. Viswanathan, K.; Omorebokhae, R.; Li, G.; Gross, R.A. Protease-catalyzed oligomerization of hydrophobic amino acid ethyl esters in homogeneous reaction media using L-phenylalanine as a model system. Biomacromolecules 2010, 11, 2152-2160.
24. Qin, X.; Xie, W.; Su, Q.; Du, W.; Gross, R.A. Protease-catalyzed oligomerization of L-lysine ethyl ester in aqueous solution. ACS Catal. 2011, 1, 1022-1034.
25. Narai-Kanayama, A.; Hanaishi, T.; Aso, K. α-Chymotrypsin-catalyzed synthesis of poly-Lcysteine in a frozen aqueous solution. J. Biotechnol. 2012, 157, 428-436.
26. Qin, X.; Xie, W.; Tian, S.; Cai, J.; Yuan, H.; Yu, Z.; Gross, R.A. Enzyme-triggered hydrogelation via self-assembly of alternating peptides. Chem. Commun. 2013, 49, 4839-4841.
27. Ageitos, J.M.; Baker, P.J.; Sugahara, M.; Numata, K. Proteinase K-catalyzed synthesis of linear and star oligo-L-phenylalanine conjugates. Biomacromolecules 2013, 14, 3635-3642.
28. Aso, K.; Kodaka, H. Trypsin-catalyzed Oligomerization of L-Lysine Esters. Biosci. Biotechnol. Biochem. 1992, 56, 755-758.
29. Aso, K.; Kodaka, H.; Fukushi, H.; Lee, H. Trypsin-catalyzed synthesis of the arginyl-arginine dipeptide from L-arginine ethyl ester. Biotechnol. Lett. 1992, 14, 451-454.
30. Hou, R.Z.; Yang, Y.; Li, G.; Huang, Y.B.; Wang, H.; Liu, Y.J.; Xu, L.; Zhang, X.Z. Synthesis of a precursor dipeptide of RGDS (Arg-Gly-Asp-Ser) catalysed by the industrial protease alcalase. Biotechnol. Appl. Biochem. 2006, 44, 73-80.
31. 2by a combination of chemical and enzymatic methods. J. Biotechnol. 2006, 125, 311-318.
32. Schwab, L.W.; Kroon, R.; Schouten, A.J.; Loos, K. Enzyme-catalyzed ring-opening polymerization of unsubstituted β-Lactam. Macromol. Rapid Commun. 2008, 29, 794-797.
33. Ménard, R.; Storer, A.C. Papain. In Handbook of Proteolytic Enzymes; Barrett, A.J., Rawlings, N.D., Woessner, J.F., Eds.; Academic Press: London, UK, 1998; pp. 555-557.
34. Berger, A.; Schechter, I. Mapping the active site of papain with the aid of peptide substrates and inhibitors. Philos. Trans. R. Soc. Lond. B Biol. Sci. 1970, 257, 249-264.
35. Kamphuis, I.G.; Drenth, J.; Baker, E.N. Thiol proteases: Comparative studies based on the high-resolution structures of papain and actinidin, and on amino acid sequence information for cathepsins B and H, and stem bromelain. J. Mol. Biol. 1985, 182, 317-329.
36. Fagerland, J.; Finne-Wistrand, A.; Numata, K. Short one-pot chemo-enzymatic synthesis of L-lysine and L-alanine diblock co-oligopeptides. Biomacromolecules 2014, 15, 735-743.
37. ∈-Protecting Groups on the Protease-Catalyzed Oligomerization of L-Lysine Methyl Ester. ACS Catal. 2014, 4, 1783-1792.
38. Rowan, A.D. Stem bromelain. In Handbook of Proteolytic Enzymes; Barrett, A.J., Rawlings, N.D., Woessner, J.F., Eds.; Academic Press: London, UK, 1998; pp. 566-567.
39. Appel, W. Chymotrypsin: Molecular and catalytic properties. Clin. Biochem. 1986, 19, 317-322.
40. Beck-Piotraschke, K.; Jakubke, H. Protease-catalysed synthesis of peptides containing histidine and lysine. Tetrahedron Asymmetry 1998, 9, 1505-1518.
41. Saenger, W. Proteinase, K. Handbook of Proteolytic Enzymes; Barrett, A.J., Rawlings, N.D., Woessner, J.F., Eds.; Academic Press: London, UK, 1998; pp. 322-325.
42. Ebeling, W.; Hennrich, N.; Klockow, M.; Metz, H.; Orth, H.D.; Lang, H. Proteinase K from Tritirachium album Limber. Eur. J. Biochem. 1974, 47, 91-97.
43. Morihara, K.; Tsuzuki, H. Specificity of proteinase K from Tritirachium album Limber for synthetic peptides. Agric. Biol. Chem. 1975, 39, 1489-1492.
44. Halfon, S.; Craik, C.S. Trypsin. In Handbook of Proteolytic Enzymes; Barrett, A.J., Rawlings, N.D., Woessner, J.F., Eds.; Academic Press: London, UK, 1998; pp. 12-21.
45. Manea, M.; Mezo, G.; Hudecz, F.; Przybylski, M. Mass spectrometric identification of the trypsin cleavage pathway in lysyl-proline containing oligotuftsin peptides. J. Pept. Sci. 2007, 13, 227-236.
46. Ballinger, M.D.; Wells, J.A. Subtilisin. In Handbook of Proteolytic Enzymes; Barrett, A.J., Rawlings, N.D., Woessner, J.F., Eds.; Academic Press: London, UK, 1998; pp. 289-294.
47. Nuijens, T.; Schepers, A.H.M.; Cusan, C.; Kruijtzer, J.A.W.; Rijkers, D.T.S.; Liskamp, R.M.J.; Quaedflieg, P.J.L.M. Enzymatic fragment condensation of side chain-protected peptides using subtilisin a in anhydrous organic solvents: A general strategy for industrial peptide synthesis. Adv. Synth. Catal. 2013, 355, 287-293.
48. Gandhi, N.N.; Patil, N.S.; Sawanta, S.B.; Joshi, J.B.; Wangikar, P.P.; Mukesh, D. Lipase-catalyzed esterification. Catal. Rev. Sci. Eng. 2000, 42, 439-480.
49. West, J.B.; Hennen, W.J.; Lalonde, J.L.; Bibbs, J.A.; Zhong, Z.; Meyer, E.F.; Wong, C. Enzymes as Synthetic Catalysts: Mechanistic and Active-Site Considerations of Natural and Modified Chymotrypsin. J. Am. Chem. Soc. 1990, 5320, 5313-5320.
50. Grünberg, R.; Domgall, I.; Günther, R.; Rall, K.; Hofmann, H.J.; Bordusa, F. Peptide bond formation mediated by substrate mimetics. Eur. J. Biochem. 2000, 267, 7024-7030.
51. Chen, K.Q.; Robinson, A.C.; van Dam, M.E.; Martinez, P.; Economou, C.; Arnold, F.H. Enzyme engineering for nonaqueous solvents. II. Additive effects of mutations on the stability and activity of subtilisin E in polar organic media. Biotechnol. Prog. 1991, 7, 125-129.
52. Salam, S.M.A.; Kagawa, K.; Kawashiro, K. α-Chymotrypsin-catalyzed peptide synthesis in frozen aqueous solution using N-protected amino acid carbamoylmethyl esters as acyl donors. Tetrahedron Asymmetry 2006, 17, 22-29.
53. Salam, S.M.A.; Kagawa, K.; Kawashiro, K. Proteasecatalyzed dipeptide synthesis from N-protected amino acid carbamoylmethyl esters and free amino acids in frozen aqueous solutions. Enzym. Microb. Technol. 2008, 43, 537-543.
54. Wehofsky, N.; Wespe, C.; Cerovsky, V.; Pech, A.; Hoess, E.; Rudolph, R.; Bordusa, F. Ionic liquids and proteases: A clean alliance for semisynthesis. Chem Bio Chem 2008, 9, 1493-1499.
55. Noritomi, H. Protease-catalyzed synthetic reactions in ionic liquids. In Ionic Liquids: Applications and Perspectives; Kokorin, A., Ed.; Intech: Rijeka, Croatia, 2011; pp. 517-528.
56. Erbeldinger, M.; Mesiano, A.J.; Russell, A.J. Enzymatic catalysis of formation of Z-aspartame in ionic liquid-An alternative to enzymatic catalysis in organic solvents. Biotechnol. Prog. 2000, 16, 1129-1131.
57. Mishima, K.; Matsuyama, K.; Baba, M.; Chidori, M. Enzymatic dipeptide synthesis by surfactant-coated α-chymotrypsin complexes in supercritical carbon dioxide. Biotechnol. Prog. 2003, 19, 281-284.
58. Noritomi, H.; Miyata, M.; Kato, S.; Nagahama, K. Enzymatic synthesis of peptide in acetonitrile/supercritical carbon dioxide. Biotechnol. Lett. 1995, 17, 1323-1328.
59. Ulijn, R.V.; Baragaña, B.; Halling, P.J.; Flitsch, S.L. Protease-catalyzed peptide synthesis on solid support. J. Am. Chem. Soc. 2002, 124, 10988-10989.
60. Klibanov, A.M. Enzyme stabilization by immobilization. Anal. Biochem. 1979, 93, 1-25.
61. Meng, L.; Joshi, R.; Eckstein, H. Application of enzymes for the synthesis of the Cholecystokinin Pentapeptide (CCK-5). Chimica Oggi Chem. Today 2006, 24, 1-4.
62. Talekar, S.; Joshi, A.; Joshi, G.; Kamat, P.; Haripurkar, R.; Kambale, S. Parameters in preparation and characterization of cross linked enzyme aggregates (CLEAs). RSC Adv. 2013, 3, 12485-12511.
63. Sheldon, R.A. Characteristic features and biotechnological applications of cross-linked enzyme aggregates (CLEAs). Appl. Microbiol. Biotechnol. 2011, 92, 467-477.
64. Nuijens, T.; Cusan, C.; Schepers, A.C.H.M.; Kruijtzer, J.A.W.; Rijkers, D.T.S.; Liskamp, R.M.J.; Quaedflieg, P.J.L.M. Enzymatic synthesis of activated esters and their subsequent use in enzyme-based peptide synthesis. J. Mol. Catal. B Enzym. 2011, 71, 79-84.
65. Bordusa, F. Nonconventional amide bond formation catalysis: Programming enzyme specificity with substrate mimetics. Braz. J. Med. Biol. Res. 2000, 33, 469-485.
66. Beer, R.J.; Zarzycka, B.; Mariman, M.; Amatdjais-Groenen, H.I.; Mulders, M.J.; Quaedflieg, P.J.; Delft, F.L.; Nabuurs, S.B.; Rutjes, F.P. Papain-specific activating esters in aqueous dipeptide synthesis. Chem Bio Chem 2012, 13, 1319-1326.
67. Bread, N.S.; Armentrout, S.A.; Weisberger, A.S. Inhibition of mammalian protein synthesis by antibiotics. Pharmacol. Rev. 1969, 21, 213-245.
68. Nathans, D. Puromycin inhibition of protein synthesis: Incorporation of puromycin into peptide chains. Proc. Natl. Acad. Sci. USA 1964, 51, 585-592.
69. Usuki, H.; Yamamoto, Y.; Arima, J.; Iwabuchi, M.; Miyoshi, S.; Nitoda, T.; Hatanaka, T. Peptide bond formation by aminolysin-A catalysis: A simple approach to enzymatic synthesis of diverse short oligopeptides and biologically active puromycins. Org. Biomol. Chem. 2011, 9, 2327-2335.
70. Thongyoo, P.; Jaulent, A.M.; Tate, E.W.; Leatherbarrow, R.J. Immobilized protease-assisted synthesis of engineered cysteine-knot microproteins. Chem Bio Chem 2007, 8, 1107-1109.
71. Rosen, M.J. Surfactants and Interfacial Phenomena, 3rd ed.; John Wiley & Sons, Inc.: New York, NY, USA, 2004.
72. Piera, E.; Infante, M.R.; Clapés, P. Chemo-enzymatic synthesis of arginine-based gemini surfactants. Biotechnol. Bioeng. 2000, 70, 323-331.
73. 2of cellular adhesion motif in low-water organic media. Enzym. Microb. Technol. 2006, 39, 1159-1165.
74. Huang, Y.B.; Xiao, Y.P.; Wang, H.; Hou, R.Z.; Zhang, N.; Wu, X.X.; Xu, L.; Zhang, X.Z. Chemo-enzymatic synthesis of tripeptide RGD diamide in organic solvents. J. Biotechnol. 2005, 116, 51-59.
75. Sun, H.; He, B.; Xu, J.; Wu, B.; Ouyang, P. Efficient chemo-enzymatic synthesis of endomorphin-1 using organicsolvent stable proteases to green the synthesis of the peptide. Green Chem. 2011, 13, 1680-1685.