The Enzyme Database

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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]
 
 


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