Phenylhydrazide as an enzyme-labile protecting group in peptide synthesis

Journal of Organic Chemistry

Volumn 67, Issue 20, 2002, Pages 6902-6910

  Völkert, Martin ^a,b   Koul, Surrinder ^c   Müller, Gernot H ^d   Lehnig, Manfred ^b   Waldmann, Herbert ^a,b  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b TU DORTMUND UNIVERSITY   (Germany)

^c CSIR INDIAN INSTITUTE OF INTEGRATIVE MEDICINE   (India)

^d Fluka Production GmbH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYMATIC CLEAVAGE;

AMINO ACIDS; BIOCATALYSTS; FREE RADICALS; HYDROLYSIS; OXYGEN; SYNTHESIS (CHEMICAL);

ENZYME KINETICS;

HYDRAZIDE DERIVATIVE; MONOPHENOL MONOOXYGENASE; PHENYLHYDRAZIDE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYST; CARBOXY TERMINAL SEQUENCE; ENZYME ACTIVITY; OXIDATION; OXYGEN SATURATION; PEPTIDE SYNTHESIS; PH; TEMPERATURE;

AGARICALES; AMINO ACIDS; CATALYSIS; CHEMISTRY, ORGANIC; ELECTRON SPIN RESONANCE SPECTROSCOPY; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; LACCASE; METHIONINE; MOLECULAR STRUCTURE; MONOPHENOL MONOOXYGENASE; OXIDATION-REDUCTION; OXIDOREDUCTASES; OXYGEN; PEPTIDES; PHENYLHYDRAZINES; TEMPERATURE;

EID: 0037019977     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0259966     Document Type: Article

References (39)

1. 2; PalCl, palmitoyl chloride.
2. Völkert, M.; Wagner, M.; Peters, C.; Waldmann, H. Biol. Chem. 2001, 382, 1133-1145.
3. Kadereit, D.; Kuhlmann, J.; Waldmann, H. ChemBioChem 2000, 1, 144-169.
4. Hinterding, K.; Alonso-Díaz, D.; Waldmann, H. Angew. Chem., Int. Ed. 1998, 37, 688-749.
5. Seitz, O.; Heinemann, I.; Mattes, A.; Waldmann, H. Tetrahedron 2001, 57, 2247-2277.
6. Kadereit, D.; Waldmann, H. Chem. Rev. 2001, 101, 3367-3396.
7. Kadereit, D.; Waldmann, H. Monatsh. Chem. 2000, 131, 571-584.
8. Sebastian, D.; Waldmann, H. Tetrahedron Lett. 1997, 38, 2927-2930.
9. Sander, J.; Waldmann, H. Chem. Eur. J. 2000, 6, 1564-1577.
10. Pohl, T.; Waldmann, H. J. Am. Chem. Soc. 1997, 119, 6702- 6710.
11. Jeyaraj, D. A.; Waldmann, H. Tetrahedron Lett. 2001, 42, 835-837.
12. Flohr, S.; Jungmann, V,; Waldmann, H. Chem. Eur. J. 1999, 5, 669-681.
13. Jeyaraj, D. A.; Prinz, H.; Waldmann, H. Chem. Eur. J. 2002, 8, 1879-1887.
14. Reents, R.; Jeyaraj, D. A.; Waldmann, H. Adv. Synth. Catal. 2001, 343, 501-513.
15. Part of the results reported in this paper were published in preliminary form in: Müller, G. H.; Waldmann, H. Tetrahedron Lett. 1999, 40, 3549-3552.
16. Milne, H. B.; Halver, J. E.; Ho, D. S.; Mason, M. S. J. Am. Chem. Soc. 1957, 79, 637-639.
17. Milne, H. B.; Kilday, W. J. Org. Chem. 1965, 30, 64-71.
18. Milne, H. B.; Carpenter, F. H. J. Org. Chem. 1968, 33, 4476-4479.
19. Milne, H. B.; Most, C. F. J. Org. Chem. 1968, 33, 169-175.
20. Semenov, A. N.; Lomonosova, I. V.; Berezin, V. I.; Titov, M. I. Biotechnol. Bioeng. 1993, 42, 1137-1141.
21. Espin, J. C.; Varón R.; Fenoll, L. G.; Gilabert, M. A.; García-Ruiz, P. A.; Tudela, J.; García-Cánovas, F. Eur. J. Biochem. 2000, 267, 1270-1279.
22. Decker, H.; Dillinger, R.; Tuczek, F. Angew. Chem., Int. Ed. 2000, 39, 1591-1595.
23. Fontecave, M.; Pierre, J. L. Coord. Chem. Rev. 1998, 170, 125-140.
24. Müller, G. H.; Lang, A.; Seithel, D. R.; Waldmann, H. Chem. Eur. J. 1998, 4, 2513-2522.
25. Kazandjian, R. Z.; Klibanov, A. M. J. Am. Chem. Soc. 1985, 107, 5448-5450.
26. Burton, S. G.; Duncan, J. R. Biotechnol. Tech. 1995, 9, 7-12.
27. Burton, S. G.; Duncan, J. R. Biotechnol. Lett. 1995, 17, 627-630.
28. 2 in neutral phosphate buffer without tyrosinase and more rapidly after tyrosinase addition. Toluenesulfonic acid phenylhydrazide decomposes spontaneously in buffer without further oxygen addition.
29. Burton, S. G. Catal. Today 1994, 22, 459-487.
30. Reszka K. J.; Chignell, C. F. Chemico-Biological Interact. 1995, 96, 223-234.
31. Additional ESR-investigations with Boc-Pro-N=N-Ph isolated after NBS-oxidation and DMPO in phosphate buffer confirm that the hydrolysis indeed occurs under formation of a phenyl radical. Interestingly, this free radical formation is slowed, but not suppressed in the presence of tyrosinase, a fact that we do not truly understand yet.
32. Pandey, G.; Muralikrishna, C.; Bhalearo, U. T. Tetrahedron Lett. 1990, 31, 3771-3774.
33. Krol, E. S.; Bolton, J. L. Chem.-Biol. Interact. 1997, 104, 11-27.
34. Sugumaran, M.; Bolton, J. L. Arch. Biochem. Biophys. 1998, 353, 207-212.
35. We thank Dr. H. Wojtasek for his helpful comments in this context.
36. The assay was performed as specified in the Sigma Quality Control Test Procedure for the enzymatic assay of laccase (EC 1.10.3.2), rev. of 03/11/97.
37. Ride, J. P. Physiol. Plant Pathol. 1980, 16, 187-196.
38. Schelhaas, M.; Nägele, E.; Kuder, N.; Bader, B.; Kuhlmann, J.; Wittinghofer, A.; Waldmann, H. Chem. Eur. J. 1999, 5, 1239-1252.
39. Nägele, E.; Schelhaas, M.; Kuder, N.; Waldmann, H. J. Am. Chem. Soc. 1998, 120, 6889-6902.