Chemical modification of enzymes for enhanced functionality

Current Opinion in Biotechnology

Volumn 10, Issue 4, 1999, Pages 324-330

  DeSantis, Grace ^a   Jones, J Bryan ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME; HYDROLASE; MACROGOL; ORGANIC SOLVENT; PEROXIDASE; PROTEIN;

BIOTECHNOLOGY; CATALYST; CHEMICAL MODIFICATION; ENZYME ACTIVITY; ENZYME MODIFICATION; ENZYME STABILITY; ENZYME STRUCTURE; PRIORITY JOURNAL; PROTEIN CROSS LINKING; REVIEW; SITE DIRECTED MUTAGENESIS; SOLUBILITY; STRUCTURE ACTIVITY RELATION;

EID: 0033178813     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0958-1669(99)80059-7     Document Type: Article

References (41)

1. Zaks A, Dodds D: Application of biocatalysts and biotransformations to the synthesis of pharmaceuticals. Drug Discov Today 1997, 2:513-531.
2. Faber K: Biotransformations in Organic Synthesis, Edn 3. Heidelberg: Springer-Verlag; 1997.
3. Polgar L, Bender ML: A new enzyme containing a synthetically formed active site. Thiolsubtilisin. J Am Chem Soc 1966, 88:3153-3154.
4. Neet KE, Koshland DE Jr: The conversion of serine at the active site of subtilisin to cysteine: A 'chemical mutation'. Proc Natl Acad Sci USA 1966, 56:1606-1611.
5. Kaiser ET: Catalytic activity of enzymes altered at their active sites. Angew Chem Int Ed Engl 1988, 27:913-922.
6. Quiocho FA, Richards FM: Intermolecular cross linking of a protein in the crystalline state: Carboxypeptidase-A. Proc Natl Acad Sci USA 1964, 52:833-839.
7. St Clair NL, Navia MA: Cross-linked enzyme crystals as robust biocatalysts. J Am Chem Soc 1992, 114:7314-7316.
8. Wang Y-F, Yakovlevsky K, Zhang B, Margolin AL: Cross-linked enzyme crystals (CLEC) of subtilisin: A versatile catalyst for organic synthesis. J Org Chem 1997, 32:3488-3495.
9. Van Unen D-J, Sakodinskaya IK, Engbersen JFJ, Reinhoudt DN: Crown ether activation of cross-linked subtilisin Carlsberg crystals in organic solvents. J Chem Soc Perkin Trans 1 1998, 20:3341-3343.
10. Kazan D, Ertan H, Erarslan A: Stabilization of Escherichia coli penicillin G acylase against thermal inactivation by cross-linking with dextran dialdehyde polymers. Appl Microbiol Biotechnol 1997, 48:191-197.
11. Venkatesh R, Sundaram PV: Modulation of stability properties of bovine trypsin after in vitro structural changes with a variety of chemical modifiers. Protein Eng 1998, 11:691-698.
12. Collins AM, Maslin C, Davis RJ: Scale-up of a chiral resolution using cross-linked enzyme crystals. Org Process Res Dev 1998, 2:400-406.
13. Lundbland RL, Bradshaw RA: Applications of site-specific chemical modification in the manufacture of biopharmaceuticals: 1. An overview. Biotechnol Appl Biochem 1997, 26:143-151.
14. Hernáiz MJ, Sánchez-Montero JM, Sinisterra JV: Influence of the nature of modifier in the enzymatic activity of chemical modified semipurified lipase from Candida rugosa. Biotechnol Bioeng 1997, 55:252-260.
15. Garcia D, Ortéga F, Marty JL: Kinetics of thermal inactivation of horseradish peroxidase: Stabilizing effect of methoxypoly (ethylene glycol). Biotechnol Appl Biochem 1998, 27:49-54.
16. Jene Q, Pearson JC, Lowe CR: Surfactant modified enzymes: Solubility and activity of surfactant-modified catalase in organic solvents. Enzyme Microb Technol 1997, 20:69-74.
17. Tinoco R, Vazquez-Duhalt R: Chemical modification of cytochrome C improves their catalytic properties in oxidation of polycyclic aromatic hydrocarbons. Enzyme Microb Technol 1998, 22:8-12.
18. Baek W-O, Vijayalakshmi MA: Effect of chemical glycosylation of RNase A on the protein stability and surface histidines accessibility in immobilized metal ion affinity electrophoresis (IMAGE) system. Biochim Biophys Acta 1997, 1336:394-402.
19. Fadnavis NW, Babu RL, Vadivel SK, Deshpande AA, Bhalerao UT: Lipase catalyzed regio- And steriospecific hydrolysis: Chemoenzymatic synthesis of both (R)- And (S)-enantiomers of α-lipoic acid. Tetrahedron - Asymmetry 1998, 9:4109-4112.
20. Wu Z-P, Hilvert D: Conversion of a protease into an acyl transferase: Selenosubtilisin. J Am Chem Soc 1989, 111:4514-4515.
21. Liu JQ, Jiand M-S, Luo G-M, Yan G-L, Shen J-C: Conversion of trypsin into a selenium containing enzyme by using chemical mutation. Biotechnol Lett 1998, 20:693-696.
22. Häring D, Schüler E, Adam W, Saha-Möller CR, Schreier P: Semisynthetic enzymes in asymmetric synthesis: Enantioselective reduction of racemic hydroperoxides catalyzed by seleno-subtilisin. J Org Chem 1999, 64:832-835.
23. Häring D, Schreier P: From detergent additive to semisynthetic peroxidase - Simplified and up-scaled synthesis of seleno- subtilisin.subtilisin. Biotechnol Bioeng 1998, 59:786-791.
24. Häring D, Schreier P: Novel biocatalysts by chemical modification of known enzymes: Cross-linked microcrystals of the semisynthetic peroxidase.
25. Sinha Roy R, Imperiali B: Pyridoxamine-amino acid chimeras in semisynthetic aminotransferase mimics. Protein Eng 1997, 10:691-698.
26. Davis RR, Distefano MD: A semisynthetic metalloenzyme based on a protein cavity that catalyzes the enantioselective hydrolysis of ester and amide substrates. J Am Chem Soc 1997, 119:11643-11652.
27. Bech LM, Breddam K: Chemical modifications of a cysteinyl residue introduced in the binding site of carboxypeptidase Y by site- directeddirected mutagenesis. Carlsberg Res Commun 1988, 53:381-393.
28. Smith HB, Larimer FW, Hartman FC: Subtle alteration of the active site ribulose bisphosphate carboxylase/oxygenase by concerted site-directed mutagenesis and chemical modification. Biochem Biophys Res Commun 1988, 152:579-584.
29. Foong LY, You S, Jaikaran DC, ZHang Z, Zunic V, Woolley GA: Development of a novel thiol reagent for probing ion channel structure: Studies in a model system. Biochemistry 1997, 11:1343-1348.
30. Grøn H, Bech LM, Branner S, Breddam K: A highly active and oxidation-resistant subtilisin-like enzyme produced by a combination of site-directed mutagenesis and chemical modification. Eur J Biochem 1990, 194:897-901.
31. 1′ pockets of subtilisin Bacillus lentus. Biochemistry 1998, 37:5968-5973.
32. Smith DJ, Maggio ET, Kenyon GL: Simple alkanethiol groups for temporary blocking of sulfhydryl groups of enzymes. Biochemistry 1975, 14:766-771.
33. Kice JL, Rogers T, Warheit AC: The relative nucleophilicity of common nucleophiles toward sulfenyl sulfur. Comparison of the relative reactivity of different nucleophiles toward sulfenyl vs. Sulfonyl sulfur. J Am Chem Soc 1974, 96:8020-8026.
34. Berglund P, De-santis G, Stabile MR, Shang X, Gold M, Bott RR, Graycar TP, Lau TH, Mitchinson C, Jones JB: Chemical modification of cysteine mutants of subtilisin Bacillus lentus can create better catalysts than the wild-type enzyme. J Am Chem Soc 1997, 119:5265-5266.
35. De-santis G, Jones JB: Chemical modifications at a single site can induce significant shifts in the pH-activity profiles of a serine protease. J Am Chem Soc 1998, 120:8582-8586.
36. Davis BG, Lloyd RC, Jones JB: Controlled site-selective glycosylation of proteins by a combined site-directed mutagenesis chemical modification approach. J Org Chem 1998, 63:9614-9615.
37. Plettner E, KHumtaveeporn K, Shang X, Jones JB: Combinatorial approach to chemical modification of subtilisin Bacillus lentus. Biorg Med Chem Lett 1998, 8:2291-2296.
38. Lloyd R, Dickman M, Jones JB: Chemically modified mutants of subtilisin Bacillus lentus catalyze transesterification reactions better than wild type. Tetrahedron - Asymmetry 1998, 9:4099-4102.
39. Fierobe H-P, Mirgorodskaya E, McGuire KA, Roepstorf P, Svensson B, Clarke AJ: Restoration of catalytic activity beyond wild-type in glucoamylase from Asperigillus awamori by oxidation of the Glue400Cys catalytic-base mutant to cysteinesulfinic acid. Biochemistry 1998, 37:3743-3752.
40. Kuang H, Distefano MD: Catalytic enantioselective reductive amination in a host-guest system based on a protein cavity. J Am Chem Soc 1998, 120:1072-1073.
41. Secundo F, SPadaro S, Carrea G, Overbeeke PLA: Optimization of Pseudomonas cepacia lipase preparations for catalysis in organic synthesis. Biotechnol Bioeng 1999, 62:554-561.