Reaction: 3'-dehydrocarminate = 1,5-anhydro-D-erythro-hex-1-en-3-ulose + kermesate
For diagram of reaction, click here
Glossary: carminate = 7-(β-D-glucopyranosyl)-3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate
kermesate = 3,5,6,8-tetrahydroxy-1-methyl-9,10-dioxo-9,10-dihydroanthracene-2-carboxylate
1,5-anhydro-D-erythro-hex-1-en-3-ulose = (2R,3R)-3,5-dihydroxy-2-(hydroxymethyl)-2,3-dihydropyran-4-one
Other name(s): carAB (gene names)
Systematic name: 3'-dehydrocarminate lyase (kermesate-forming)
Comments: Requires Mg2+. This enzyme, isolated from the bacterium Microbacterium 5-2b, participates in a carminate degradation pathway. Following the activity of EC 1.1.3.50, C-glycoside oxidase, it cleaves the C—C bond in 3'-dehydrocarminate. The sugar moiety is released lacking a hydroxyl at position 1, and containing a double bond between C-1 and C-2. The enzyme shows weak activity with other 3'-dehydro-C-glucosides.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number:
References:
1. Mori, T., Kumano, T., He, H., Watanabe, S., Senda, M., Moriya, T., Adachi, N., Hori, S., Terashita, Y., Kawasaki, M., Hashimoto, Y., Awakawa, T., Senda, T., Abe, I. and Kobayashi, M. C-Glycoside metabolism in the gut and in nature: Identification, characterization, structural analyses and distribution of C-C bond-cleaving enzymes. Nat. Commun. 12 (2021) 6294. [PMID: 34728636]