Light activated acyl-enzymes

Details Light activated acyl-enzymes Light activated acyl-enzymes

1989-08-29

1992-05-19

Lee, Lester L.

Chemistry: molecular biology and microbiology

Treatment of micro-organisms or enzymes with electrical or...

Modification of viruses

435213, 435214, 435215, 435216, 435217, C12N 1300, C12N 976, C12N 970, C12N 968

Patent

active

051148510

ABSTRACT:
Light activated acyl-enzymes of the formula: ##STR1## are disclosed. In the compounds of Formula (III), ENZ is an enzyme, X is O or S, Y is --NR.sub.3 R.sub.4, --OR.sub.5, or --SR.sub.5, and Z is a nucleophile. m is 0 to 3 and n is 1 or 2. Y is substituted on the ring at either or both of the 4 and 6 position.
R.sub.1 and R.sub.2 are each independently H, C1 to C4 alkyl, C3 to C4 unconjugated alkenyl, or C3 to C4 unconjugated alkynyl.
R.sub.3 and R.sub.4 are each independently H, C1 to C4 alkyl, C3 to C4 unconjugated alkenyl, or C3 to C4 unconjugated alkynyl, except that R.sub.3 and R.sub.4 are not simultaneously both H. R.sub.5 is C1 to C4 alkyl, C3 to C4 unconjugated alkenyl, or C3 to C4 unconjugated alkynyl.
Methods of using the acyl-enzymes and intermediates for making the acyl-enzymes are disclosed. A preferred intermediate is 2-Propenoic acid, 3-(2-hydroxy-4-diethylaminophenyl)-2-methyl-, 4-(aminoiminomethyl)phenyl ester,(E)-, monohydrochloride salt, which is preferably reacted with thrombin to form an acyl-thrombin.

REFERENCES:
Berezin, I. V. et al., "Detection of Light Signals by Microencapsulated cis-cinnamoyl Chymotrypsin," Enzyme Microb. Technol. 2, 150 (1980).
Berezin, I. V. et al., "A Flash-Induced Reaction of a Synthetic Light-Sensitive Substrate with .alpha.-chymotrypsin," Febs Letters 8, No. 4, 173 (1970).
Kazanskaya, N. F. et al., "Autocatalytic Enzyme System for Amplification of Light Signals," Enzyme Microb. Technol. 5, 209 (1983).
Martinek, K. and Berenzin, I. V., "Artificial Light-Sensitive Enzymatic Systems as Chemical Amplifiers of Weak Light Signals," Photochemistry and Photobiology 29, 637 (1979).
McClelland, R. et al., "The Hydrolysis of Coumarin Diethyl Acetal and the Lactonization of Coumarinic Acid Ethyl Ester. The Partitioning of Tetrahedral Intermediates Generated from Independent Source," Can. J. Chem. 57, 2260 (1979).
Turner, A. D. et al., "Photoreactivation of Irreversibly Inhibited Serine Proteinases, " J. Am. Chem. Soc. 110, 244 (1988).
Turner, A. D. et al., "Photochemical Activation of Acylated .alpha.-Thrombin," J. Am. Chem. Soc. 109, 1274 (1987).
Varfolomeyev, S. D. et al., "Light-Initiated Enzymic Activity Caused by Photostereoisomerization of Cis-4-Nitrocinnamoyl-.alpha.-Chymotrypsin," Febs Letters 15, No. 2, 118 (1971).

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