The Enzyme Database

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EC 1.1.1.362     
Accepted name: aklaviketone reductase
Reaction: aklavinone + NADP+ = aklaviketone + NADPH + H+
For diagram of aflatoxin biosynthesis, click here
Glossary: aklavinone = methyl (1R,2R,4S)-2-ethyl-2,4,5,7-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
aklaviketone = methyl (1R,2R)-2-ethyl-2,5,7-trihydroxy-4,6,11-trioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
Other name(s): dauE (gene name); aknU (gene name)
Systematic name: aklavinone:NADP+ oxidoreductase
Comments: The enzyme is involved in the synthesis of the aklavinone aglycone, a common precursor for several anthracycline antibiotics including aclacinomycins, daunorubicin and doxorubicin. The enzyme from the Gram-negative bacterium Streptomyces sp. C5 produces daunomycin.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Dickens, M.L., Ye, J. and Strohl, W.R. Cloning, sequencing, and analysis of aklaviketone reductase from Streptomyces sp. strain C5. J. Bacteriol. 178 (1996) 3384–3388. [DOI] [PMID: 8655529]
[EC 1.1.1.362 created 2013]
 
 
EC 1.14.13.180     
Accepted name: aklavinone 12-hydroxylase
Reaction: aklavinone + NADPH + H+ + O2 = ε-rhodomycinone + NADP+ + H2O
For diagram of aflatoxin biosynthesis, click here
Glossary: aklavinone = methyl (1R,2R,4S)-2-ethyl-2,4,5,7-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
ε-rhodomycinone = methyl (1R,2R,4S)-2-ethyl-2,4,5,7,12-pentahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
Other name(s): DnrF; RdmE; aklavinone 11-hydroxylase (incorrect)
Systematic name: aklavinone,NADPH:oxygen oxidoreductase (12-hydroxylating)
Comments: The enzymes from the Gram-positive bacteria Streptomyces peucetius and Streptomyces purpurascens participate in the biosynthesis of daunorubicin, doxorubicin and rhodomycins. The enzyme from Streptomyces purpurascens is an FAD monooxygenase.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Filippini, S., Solinas, M.M., Breme, U., Schluter, M.B., Gabellini, D., Biamonti, G., Colombo, A.L. and Garofano, L. Streptomyces peucetius daunorubicin biosynthesis gene, dnrF: sequence and heterologous expression. Microbiology 141 (1995) 1007–1016. [DOI] [PMID: 7773378]
2.  Niemi, J., Wang, Y., Airas, K., Ylihonko, K., Hakala, J. and Mantsala, P. Characterization of aklavinone-11-hydroxylase from Streptomyces purpurascens. Biochim. Biophys. Acta 1430 (1999) 57–64. [DOI] [PMID: 10082933]
[EC 1.14.13.180 created 2013]
 
 
EC 2.4.1.326     
Accepted name: aklavinone 7-L-rhodosaminyltransferase
Reaction: dTDP-β-L-rhodosamine + aklavinone = dTDP + aclacinomycin T
For diagram of aklavinone biosynthesis, click here
Glossary: dTDP-β-L-rhodosamine = dTDP-2,3,6-trideoxy-3-dimethylamino-β-L-lyxo-hexose
aklavinone = methyl (1R,2R,4S)-2-ethyl-2,4,5,7-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
aclacinomycin T = 7-O-(α-L-rhodosaminyl)aklavinone
Other name(s): AknS/AknT; aklavinone 7-β-L-rhodosaminyltransferase; dTDP-β-L-rhodosamine:aklavinone 7-α-L-rhodosaminyltransferase
Systematic name: dTDP-β-L-rhodosamine:aklavinone 7-α-L-rhodosaminyltransferase (configuration-inverting)
Comments: Isolated from the bacterium Streptomyces galilaeus. Forms a complex with its accessory protein AknT, and has very low activity in its absence. The enzyme can also use dTDP-2-deoxy-β-L-fucose. Involved in the biosynthesis of other aclacinomycins.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Lu, W., Leimkuhler, C., Gatto, G.J., Jr., Kruger, R.G., Oberthur, M., Kahne, D. and Walsh, C.T. AknT is an activating protein for the glycosyltransferase AknS in L-aminodeoxysugar transfer to the aglycone of aclacinomycin A. Chem. Biol. 12 (2005) 527–534. [DOI] [PMID: 15911373]
2.  Leimkuhler, C., Fridman, M., Lupoli, T., Walker, S., Walsh, C.T. and Kahne, D. Characterization of rhodosaminyl transfer by the AknS/AknT glycosylation complex and its use in reconstituting the biosynthetic pathway of aclacinomycin A. J. Am. Chem. Soc. 129 (2007) 10546–10550. [DOI] [PMID: 17685523]
[EC 2.4.1.326 created 2014, modified 2015]
 
 
EC 2.4.1.327     
Accepted name: aclacinomycin-T 2-deoxy-L-fucose transferase
Reaction: dTDP-2-deoxy-β-L-fucose + aclacinomycin T = dTDP + aclacinomycin S
For diagram of aclacinomycin A and Y biosynthesis, click here
Glossary: idarubicin = (7S,9S)-9-acetyl-7-(3-amino-2,3,6-trideoxy-β-L-lyxo-hexosyloxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione
aclacinomycin S = 7-O-(2-deoxy-α-L-fucosyl-(1→4)-rhodosaminyl)aklavinone
aclacinomycin T = 7-O-(α-L-rhodosaminyl)aklavinone
Other name(s): AknK
Systematic name: dTDP-2-deoxy-β-L-fucose:7-(α-L-rhodosaminyl)aklavinone 2-deoxy-α-L-fucosyltransferase
Comments: The enzyme, isolated from the bacterium Streptomyces galilaeus, is involved in the biosynthesis of other aclacinomycins. Also acts on idarubicin. It will slowly add a second 2-deoxy-L-fucose unit to aclacinomycin S in vitro.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Lu, W., Leimkuhler, C., Oberthur, M., Kahne, D. and Walsh, C.T. AknK is an L-2-deoxyfucosyltransferase in the biosynthesis of the anthracycline aclacinomycin A. Biochemistry 43 (2004) 4548–4558. [DOI] [PMID: 15078101]
[EC 2.4.1.327 created 2014]
 
 
EC 3.1.1.95     
Accepted name: aclacinomycin methylesterase
Reaction: aclacinomycin T + H2O = 15-demethylaclacinomycin T + methanol
For diagram of aflatoxin biosynthesis, click here
Glossary: aclacinomycin T = 2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-{[2,3,6-trideoxy-3-(dimethylamino)-α-L-lyxo-hexopyranosyl]oxy}-1-naphthacenecarboxylic acid methyl ester = methyl (1R,2R,4S)-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-4-{[2,3,6-trideoxy-3-(dimethylamino)-α-L-lyxo-hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
15-demethoxyaclacinomycin T = (1R,2R,4S)-2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-{[2,3,6-trideoxy-3-(dimethylamino)-α-L-lyxo-hexopyranosyl]oxy}-1-naphthacenecarboxylic acid = (1R,2R,4S)-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-4-{[2,3,6-trideoxy-3-(dimethylamino)-α-L-lyxo-hexopyranosyl]oxy}-1,2,3,4,6,11-hexahydrotetracene-1-carboxylic acid
Other name(s): RdmC; aclacinomycin methyl esterase
Systematic name: aclacinomycin T acylhydrolase
Comments: The enzyme is involved in the modification of the aklavinone skeleton in the biosynthesis of anthracyclines in Streptomyces species.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Wang, Y., Niemi, J., Airas, K., Ylihonko, K., Hakala, J. and Mantsala, P. Modifications of aclacinomycin T by aclacinomycin methyl esterase (RdmC) and aclacinomycin-10-hydroxylase (RdmB) from Streptomyces purpurascens. Biochim. Biophys. Acta 1480 (2000) 191–200. [DOI] [PMID: 11004563]
2.  Jansson, A., Niemi, J., Mantsala, P. and Schneider, G. Crystal structure of aclacinomycin methylesterase with bound product analogues: implications for anthracycline recognition and mechanism. J. Biol. Chem. 278 (2003) 39006–39013. [DOI] [PMID: 12878604]
[EC 3.1.1.95 created 2013]
 
 
EC 5.5.1.23     
Accepted name: aklanonic acid methyl ester cyclase
Reaction: aklaviketone = methyl aklanonate
For diagram of aklavinone biosynthesis, click here
Glossary: aklaviketone = methyl (1R,2R)-2-ethyl-2,5,7-trihydroxy-4,6,11-trioxo-1,2,3,4,6,11-hexahydrotetracene-1-carboxylate
methyl aklanonate = methyl [4,5-dihydroxy-9,10-dioxo-3-(3-oxopentanoyl)-9,10-dihydroanthracen-2-yl]acetate
Other name(s): dauD (gene name); aknH (gene name); dnrD (gene name); methyl aklanonate cyclase; methyl aklanonate-aklaviketone isomerase (cyclizing); aklaviketone lyase (decyclizing)
Systematic name: aklaviketone lyase (ring-opening)
Comments: The enzyme is involved in the biosynthesis of aklaviketone, an intermediate in the biosynthetic pathways leading to formation of several anthracycline antibiotics, including aclacinomycin, daunorubicin and doxorubicin.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Dickens, M.L., Ye, J. and Strohl, W.R. Analysis of clustered genes encoding both early and late steps in daunomycin biosynthesis by Streptomyces sp. strain C5. J. Bacteriol. 177 (1995) 536–543. [DOI] [PMID: 7836284]
2.  Kendrew, S.G., Katayama, K., Deutsch, E., Madduri, K. and Hutchinson, C.R. DnrD cyclase involved in the biosynthesis of doxorubicin: purification and characterization of the recombinant enzyme. Biochemistry 38 (1999) 4794–4799. [DOI] [PMID: 10200167]
3.  Kallio, P., Sultana, A., Niemi, J., Mantsala, P. and Schneider, G. Crystal structure of the polyketide cyclase AknH with bound substrate and product analogue: implications for catalytic mechanism and product stereoselectivity. J. Mol. Biol. 357 (2006) 210–220. [DOI] [PMID: 16414075]
[EC 5.5.1.23 created 2013, modified 2014]
 
 


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