Model sclerotization studies. 4. Generation of N-acetylmethionyl catechol adducts during tyrosinase-catalyzed oxidation of catechols in the presence of N-acetylmethionine

Archives of Insect Biochemistry and Physiology

Volumn 38, Issue 1, 1998, Pages 44-52

  Sugumaran, Manickam ^a   Nelson, Eroica ^a  

^a UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

Author keywords

Aryl amino acid adducts; Cuticular sclerotization; Post translational modification; Quinone tanning

Indexed keywords

4 METHYLCATECHOL; 4-METHYLCATECHOL; CATECHOL DERIVATIVE; DOPAMINE; DRUG DERIVATIVE; METHIONINE; MONOPHENOL MONOOXYGENASE; N ACETYLDOPAMINE; N ACETYLMETHIONINE; N-ACETYLDOPAMINE; N-ACETYLMETHIONINE; NEUROPROTECTIVE AGENT; QUINONE DERIVATIVE;

ANIMAL; ARTICLE; BASIDIOMYCETES; CHEMISTRY; ENZYMOLOGY; FLY; GEL CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; LEPIDOPTERA; METABOLISM; OXIDATION REDUCTION REACTION; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; BASIDIOMYCOTA; CATECHOLS; CHROMATOGRAPHY, GEL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIPTERA; DOPAMINE; MANDUCA; METHIONINE; MONOPHENOL MONOOXYGENASE; NEUROPROTECTIVE AGENTS; OXIDATION-REDUCTION; QUINONES; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0031617320     PISSN: 07394462     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-6327(1998)38:1<44::AID-ARCH5>3.0.CO;2-V     Document Type: Article

References (40)

1. Andersen SO, Roepstorff P (1982): Sclerotization of insect cuticle. III. An unsaturated derivative of N-acetyldopamine and its role in sclerotization. Insect Biochem 12:269-276.
2. Andersen SO, Peter MG, Roepstorff P (1992): Cuticle catalyzed coupling between N-acetylhistidine and N-acetyldopamine. Insect Biochem Mol Biol 22:459-469.
3. Andersen SO, Hojrup P, Roepstorff P (1995): Insect cuticular proteins. Insect Biochem Mol Biol 25:153-176.
4. Andersen SO, Peter MG, Roepstorff P (1996): Cuticular sclerotization in insects. Comp Biochem Physiol 113B:689-705.
5. Andersen SO, Jacobsen JP, Roepstorff P, Peter MG (1991): Catecholamine-protein conjugates: Isolation of an adduct of N-acetylhistidine to the side chain of N-acetyldopamine from an insect-enzyme catalyzed reaction. Tetrahedron Lett. 32:4287-4290.
6. Beck G, Cardinale S, Wang L, Reiner M, Sugumaran M (1996): Characterization of a defense complex consisting of interleukin 1 and phenoloxidase from the hemolymph of the tobacco hornworm, Manduca sexta. J Biol Chem 271:11035-11038.
7. Gupta MN, Vithayathil PJ (1980): Chemical modification of ribonuclease A with o-benzoquinone. Int J Peptide Protein Res 15:236-242.
8. Gupta MN, Vithayathil PJ (1982): Isolation and characterization of a methionine adduct of dopa-o-quinone. Bioorg Chem 11:101-107.
9. Gupta MN, Murthy GS, Vithayathil PJ (1980): o-Benzoquinone - A reagent for determining conformational differences in related proteins. Int J Peptide Protein Res 15:243-247.
10. Hall M, Scott T, Sugumaran M, Soderhall K, Law JH (1995): Prophenoloxidase from the hawkmoth Manduca sexta. Purification, activation, substrate specificity of the active enzyme and molecular cloning. Proc Natl Acad Sci USA 92:7769-7773.
11. Hopkins TL, Kramer KJ (1992): Insect cuticle sclerotization. Annu Rev Entomol 37:273-302.
12. Lipke H, Sugumaran M, Henzel W (1983): Mechanisms of sclerotization in dipterans. Adv Insect Physiol 17:1-84.
13. Pryor MGM (1940a): On the hardening of Ootheca of Blatta orientalis. Proc R Soc Lond B 128:378-393.
14. Pryor MGM (1940b): On the hardening of insect cuticle. Proc R Soc Lond B 128:393-407.
15. Ricketts D, Sugumaran M (1994): 1,2-dehydro-N-β-alanyldopamine as a new intermediate in insect cuticular sclerotization. J Biol Chem 269:22217-22221.
16. Saul SJ, Sugumaran M (1988): A novel quinone: Quinone methide isomerase generates quinone methides in insect cuticle. FEBS Lett 237:155-158.
17. Saul SJ, Sugumaran M (1989a): Characterization of a new enzyme system that desaturates the side chain of N-acetyldopamine. FEBS Lett 251:69-73.
18. Saul SJ, Sugumaran M (1989b): N-Acetyldopaminc quinone methide/1,2-dehydro-N-acetyldopamine tautomerase - A new enzyme involved in sclerotization of insect cuticle. FEBS Lett 255:340-344.
19. Saul SJ, Sugumaran M (1990a): Biosynthesis of dehydro-N-acetyldopamine by a soluble enzyme preparation from the larval cuticle of Sarcophaga bullata involves intermediary formation of N-acetyldopamine quinone and N-acetyldopmaine quinone methide. Arch Insect Biochem Physiol 15:237-254.
20. Saul SJ, Sugumaran M (1990b): 4-Alkyl-o-quinone/2-hydroxy-p-quinone methide isomerase from the larvae hemolymph of Sarcophaga bullata. I. Purification and characterization of enzyme catalyzed reaction. J Biol Chem 265:16992-16999.
21. Saul SJ, Dali H, Sugumaran M (1991): Quinone and quinone methide as transient intermediates involved in the side chain hydroxylation of N-acetyldopamine derivative by soluble enzyme from Manduca sexta cuticle. Arch Insect Biochem Physiol 16:123-137.
22. 15N NMR. Science 235:1200-1204.
23. Sugumaran M (1987): Quinone methide sclerotization - A revised mechanism for β-sclerotization of insect cuticle. Bioorg Chem 15:194-211.
24. Sugumaran M (1988): Molecular mechanisms for cuticular sclerotization. Adv Insect Physiol 21:179-231.
25. Sugumaran M (1991): Molecular mechanisms of sclerotization. In Binnington K, Retnakaran A (eds): Physiology of the Insect Epidermis. Camberra, Victoria, Australia: CSIRO Publications, pp 141-168.
26. Sugumaran M (1998): Unified mechanism for sclerotization of insect cuticle. Adv Insect Physiol 27:229-334.
27. Sugumaran M, Lipke H (1982): Crosslink precursors for the dipteran puparium. Proc Natl Acad Sci USA 79:2480-2484.
28. Sugumaran M, Ricketts D (1995): Model sclerotization studies. 3. Cuticular enzyme catalyzed oxidation of peptidyl model tyrosine and dopa derivatives. Arch Insect Biochem Physiol 28:17-32.
29. Sugumaran M, Henningan B, O'Brien J (1987): Tyrosinase catalyzed protein polymerization as an in vitro model for sclerotization of insect cuticle. Arch Insect Biochem Physiol 6:9-25.
30. Sugumaran M, Saul SJ, Semensi V (1988): On the mechanism of formation of N-acetyldopamine quinone methide in insect cuticle. Arch Insect Biochem Physiol 9:269-281.
31. Sugumaran M, Dali H, Semensi V (1989): Chemical and cuticular phenoloxidase mediated synthesis of cysteinyl catechol adducts. Arch Insect Biochem Physiol 11:127-137.
32. Sugumaran M, Schinkmann K, Bedell-Hogan D, Dali H (1990): Mechanism of activation of 1,2-dehydro-N-acetyldopamine for cuticular sclerotization. Arch Insect Biochem Physiol 14:95-112.
33. Sugumaran M, Linda B, Kundzicz H, Saul SJ, Semensi V (1992a): Studies on the enzymes involved in puparial cuticle sclerotization of Drosophila melanogaster. Arch Insect Biochem Physiol 19:271-283.
34. Sugumaran M, Semensi V, Kalyanaraman B, Bruce JM, Land EJ (1992b): Evidence for the formation of quinone methide during the oxidation of the insect cuticular sclerotizing precursor, 1,2-dehydro-N-acetyldopamine. J Biol Chem 267:10355-10361.
35. Thompson DC, Thompson JA, Sugumaran M, Moldeus P (1993): Biological and toxicological consequences of quinone methide formation. Chem Biol Interact 86: 129-162.
36. Vithayathil PJ, Gupta MN (1981): Reaction of methionine with some biologically important o-quinones. Indian J Biochem Biophys 18:82-83.
37. Vithayathil PJ, Murthy GS (1972): New reaction of o-benzoquinone at the thioether group of methionine. Nature 236:101-103.
38. Wang SX, Mure M, Medzihradszky KF, Burlingame AI, Brown DE, Dooley DM, Smith AJ, Kagan HM, Klinman JP (1996): A crosslinked cofactor in lysyl oxidase: Redox function for amino acid side chains. Science 273:1078-1084.
39. Xu R, Huang X, Morgan TD, Prakash O, Kramer K, Hawley MD (1996): Characterization of products from the reactions of N-acetyldopamine quinone with the N-acetylhistidine. Arch Biochem Biophys 329:56-64.
40. Xu R, Huang X, Hopkins TI, Kramer KJ (1997): Catecholamine and histidyl protein crosslinked structures in sclerotized insect cuticle. Insect Biochem Mol Biol 27:101-108.