Synthesis of dipeptides by suspension-to-suspension conversion via thermolysin catalysis: From analytical to preparative scale

Journal of Peptide Science

Volumn 3, Issue 4, 1997, Pages 245-251

  Eichhorn, U ^b   Bommarius, A S ^b   Drauz, K ^b   Jakubke, H D ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b EVONIK INDUSTRIES AG   (Germany)

Author keywords

Enzyme; Peptide synthesis; Substrate pool

Indexed keywords

DIPEPTIDE; THERMOLYSIN;

ARTICLE; CATALYSIS; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS;

CATALYSIS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIPEPTIDES; THERMOLYSIN;

EID: 0031181814     PISSN: 10752617     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1387(199707)3:4<245::AID-PSC98>3.0.CO;2-L     Document Type: Article

References (40)

1. K. Drauz, W. Jahn and M. Schwarm (1995). Synthesis of (R)-tert-leucinol by classical resolution of the racemic mixture. Chem. Eur. J. 1, 538-540.
2. G. A. Homandberg, J. A. Mattis and M. J. Laskowski (1978). Synthesis of peptide bonds by proteinases. Addition of organic cosolvents shifts peptide bond equilibria toward synthesis. Biochemistry 17, 5220-5227.
3. P. Kuhl, A. Könnecke, G. Doling, H. Däumer and H.-D. Jakubke (1980). Enzyme-catalyzed peptide synthesis in biphasic aqueous-organic systems. Tetrahedron Lett. 21, 893-896.
4. P. Kuhl, S. Posselt and H.-D. Jakubke (1981). α-Chymotrypsinkatalysierte Synthese von Tripeptidamiden im wäβrig-organischen Zweiphasensystem. Pharmazie 36, 463-465.
5. K. Martinek, A. N. Semenow and I. V. Berezin (1981). Enzymic synthesis in biphasic aqueous-organic systems. I. Chemical equilibrium shift. Biochim. Biophys. Acta 658 (1), 76-89.
6. K. Martinek and A. N. Semenow (1981). Enzymic synthesis in biphasic aqueous-organic systems. II. Shift of ionic equilibriums. Biochim. Biophys. Acta. Acta 658 (1), 90-101.
7. K. Oyama, S. Nishimura, Y. Nonaka, K. Kihara and T. J. Hashimoto (1981). Synthesis of an Aspartame precursor by immobilized thermolysin in an organic solvent. J. Org. Chem. 46, 5241-5242.
8. P. Kuhl, A. Wilsdorf and H.-D. Jakubke (1983). Modelluntersuchungen zur pepsin-katalysierten Peptidsynthese im wäβrig-organischen Zweiphasensystem. Monatsh. Chem. 114, 571-579.
9. Y. L. Kmel'nitski, F. K. Dien, A. N. Semenow, K. Martinek, B. Veruovic and V. Kubánek (1984). Optimization of enzyme catalysed peptide synthesis in a 'water-water immiscible organc solvent'. Tetrahedron 40, 4425-4432.
10. P. Lüthi and L. Luisi (1984). Enzymatic synthesis of hydrocarbon-soluble peptides with reverse micelles. J. Am. Chem. Soc. 106, 7285-7286.
11. C. F. Barbas, J. R. Matos, J. B. West and C.-H. Wong (1988). A search for peptide ligase: Cosolvent-mediated conversion of proteases to esterases for irreversible synthesis of peptides. J. Am. Chem. Soc. 110, 5162-5166.
12. L. R. Butler (1979). Enzymes in non-aqueous solvents. Enzyme Microbiol. Technol. 1, 253-259.
13. C. Laane, J. Tramper and M. D. Lilly, Eds.: Biocatalysis in Organic Media, Elsevier Science, Amsterdam 1987.
14. M. Reslow, P. Adlercreutz and B. Mattiasson (1987). Organic solvents for bioorganic synthesis. 1. Optimization of parameters for chymotrypsin catalyzed process. Appl. Microbiol. Biotechnol. 26, 1-8.
15. C. Tanford: Physical Chemistry of Macromolecules, John Wiley, New York 1961.
16. G. E. Schulz and R. H. Schirmer: Principles of Protein Structure, Springer Verlag, New York 1979.
17. D. S. Clark and J. E. Bailey (1984). Deactivation of α-chymotrypsin and α-chymotrypsin-CNBr-Sepharose $B conjugates in aliphatic alkohols. Biochim. Biophys. Acta. 788, 181-188.
18. P. J. Hailing, U. Eichhorn, P. Kuhl and H.-D. Jakubke (1995). Thermodynamics of solid-to-solid-conversion and application to enzymic peptide synthesis. Enzyme Microbiol. Technol. 17, 601-606.
19. R. López-Fandiño, I. Gill and E. N. Vulfson (1994). Enzymatic catalysts in heterogeneous mixtures of substrates: The role of the liquid phase and the effects of 'adjuvants'. Biotechnol. Bioeng. 43, 1016-1023.
20. M. P. Bemquerer, F. C. Theobaldo and M. Tominaga (1991). Pepsin-catalyzed peptide synthesis in biphasic systems. Biomed. Biochim. Acta 50, 94-97.
21. V. Čeřovskỳ (1992). Protease-catalyzed peptide synthesis in solvent-free system. Biotechnol. Tech. 6, 155-160.
22. I. Gill and E. N. Vulfson (1993). Enzymatic synthesis of short peptides in heterogeneous mixtures of substrates. J. Am. Chem. Soc. 115, 3348-3349.
23. P. Kuhl, U. Eichhorn and H.-D. Jakubke in: Biocatalysis in Non-conventional Media: Proc. Int. Symp. Noordwijkerhout, J. Tramper, M. H. Vermüe, H. H. Beeftink and U. von Stockar, Ed., p. 513-518, Elsevier Science, Amsterdam 1992.
24. P. Kuhl, P. J. Halling and H.-D. Jakubke (1990). Chymotrypsin suspended in organic solvents with salt hydrates is a good catalyst for peptide synthesis from mainly undissolved reactants. Tetrahedron Lett. 31, 5213-5216.
25. R. López-Fandiño, I. Gill and E. N. Vulfson (1994). Protease-catalyzed synthesis of oligopeptides in heterogeneous substrates mixtures. Biotechnol. Bioeng. 43, 1024-1030.
26. 2 (Antho-KAmide), a novel neuropeptide from sea anemones. Biochem. Biophys. Res. Comm. 179, 1205-1211.
27. K. Morihara and H. Tsuzuki (1970). Thermolysin: Kinetic study with oligopeptides. Eur. J. Biochem. 15, 374-380.
28. M. Poszgay, C. Michaud, M. Liebman and M. Orlowski (1986). Substrate and inhibitor studies of thermolysin-like neutral metalloendopeptidase from kidney membrane fractions. Comparison with bacterial thermolysin. Biochemistry 25, 1292-1299.
29. Y. Imaoka, T. Kawamoto, M. Ueda and A. Tanaka (1994). Peptide synthesis with halophenylalanines by thermolysin. Appl. Microbiol. Biotechnol. 40, 653-656.
30. M. C. Izquierdo and R. L. Stein (1990). Mechanistic studies of thermolysin. J. Am. Chem. Soc. 112 (16), 6054-6062.
31. A. F. Monzingo and B. W. Matthews (1984). Binding of N-Carboxymethyl dipeptide inhibitors to thermolysin determined by X-ray crystallography: A novel class of transition state analogues for zinc peptidases. Biochemistry 23 (24), 5724-5729.
32. D. G. Hangauser, A. F. Monzingo and B. W. Matthews (1984). An interactive computer graphics study of thermolysin-catalyzed peptide cleavage and inhibition by N-carboxzymethyl dipeptides. Biochemistry 23 (24), 5730-5741.
33. L. Riechmann and V. Kasche (1986). Reaction mechanism, specificity and pH-dependence of peptide synthesis catalyzed by the metalloproteinase thermolysin. Blochem. Biophys. Acta 872, 269-276.
34. W. R. Kester and B. W. Matthews (1977). Crystallographic study of the binding of dipeptide inhibitors to thermolysin: Implications for the mechanism of catalysis. Biochemistry 16, 2506-2516.
35. J. I. Oku and S. Inoue (1981). Asymmetric cyanohydrin synthesis catalysed by a synthetic cyclic dipeptide. J. Chem. Soc. Chem. Comm., 229-230.
36. K. Tanaka, M. Atsunori and S. Inoue (1990). The cyclic dipeptide cyclo[(S)-phenylalanyl-(S)-histidyl-] as a catalyst for asymmetric addition of hydrogen cyanide to aldehydes. J. Org. Chem. 55 (1), 181-185.
37. W. Becker, H. Freund and E. Pfeil (1965). Stereospecific synthesis of D-hydroxy nitriles and optically active ehtanolamines. Angew. Chem. Int. Ed. Engl. 4, 1079.
38. J. D. Elliot, V. M. F. Choi and W. S. Johnson (1983). Asymmetric synthesis via acetal templates. 5. Reactions with cyanotrimethysilane. Enantioselective preparations of cyanhydrins and derivatives. J. Org. Chem. 48 (13), 2294-2295.
39. T. Ziegler, B. Hörsch and F. Effenberger (1990). Ein einfacher Zugang zu (R)-α-Hydroxycarbonsäuren und (R)-1-Amino-2-alkoholen aus (R)-Cyanhydrinen. Synthesis (7), 575-578.
40. J. Brussee, E. C. Roos and A. Van Der Gen (1988). Bioorganic synthesis of optically active cyanohydrins and acyloins. Tetrahedron Lett. 29 (35), 4485-4488.