PMID- 27874239 OWN - NLM STAT- MEDLINE DCOM- 20180829 LR - 20190110 IS - 1521-3773 (Electronic) IS - 1433-7851 (Linking) VI - 55 IP - 50 DP - 2016 Dec 12 TI - Biocatalytic Properties and Structural Analysis of Phloroglucinol Reductases. PG - 15531-15534 LID - 10.1002/anie.201607494 [doi] AB - Phloroglucinol reductases (PGRs) are involved in anaerobic degradation in bacteria, in which they catalyze the dearomatization of phloroglucinol into dihydrophloroglucinol. We identified three PGRs, from different bacterial species, that are members of the family of NAD(P)H-dependent short-chain dehydrogenases/reductases (SDRs). In addition to catalyzing the reduction of the physiological substrate, the three enzymes exhibit activity towards 2,4,6-trihydroxybenzaldehyde, 2,4,6-trihydroxyacetophenone, and methyl 2,4,6-trihydroxybenzoate. Structural elucidation of PGRcl and comparison to known SDRs revealed a high degree of conservation. Several amino acid positions were identified as being conserved within the PGR subfamily and might be involved in substrate differentiation. The results enable the enzymatic dearomatization of monoaromatic phenol derivatives and provide insight into the functional diversity that may be found in families of enzymes displaying a high degree of structural homology. CI - (c) 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. FAU - Conradt, David AU - Conradt D AUID- ORCID: 0000-0001-8984-7694 AD - Institut fur Pharmazeutische Wissenschaften, Albert-Ludwigs-Universitat Freiburg, Albertstrasse 25, 79104, Freiburg, Germany. FAU - Hermann, Bianca AU - Hermann B AD - Institut fur Biochemie, Albert-Ludwigs-Universitat Freiburg, Albertstrasse 21, 79104, Freiburg, Germany. FAU - Gerhardt, Stefan AU - Gerhardt S AUID- ORCID: 0000-0002-9098-8475 AD - Institut fur Biochemie, Albert-Ludwigs-Universitat Freiburg, Albertstrasse 21, 79104, Freiburg, Germany. FAU - Einsle, Oliver AU - Einsle O AD - Institut fur Biochemie, Albert-Ludwigs-Universitat Freiburg, Albertstrasse 21, 79104, Freiburg, Germany. FAU - Muller, Michael AU - Muller M AUID- ORCID: 0000-0002-2742-4992 AD - Institut fur Pharmazeutische Wissenschaften, Albert-Ludwigs-Universitat Freiburg, Albertstrasse 25, 79104, Freiburg, Germany. LA - eng PT - Journal Article DEP - 20161122 PL - Germany TA - Angew Chem Int Ed Engl JT - Angewandte Chemie (International ed. in English) JID - 0370543 RN - 0 (Acetophenones) RN - 0 (Benzaldehydes) RN - 623D3XG80C (methyl gallate) RN - 632XD903SP (Gallic Acid) RN - 8L7XD8830T (2,4,6-trihydroxyacetophenone) RN - EC 1.3.- (Oxidoreductases Acting on CH-CH Group Donors) RN - EC 1.3.1.57 (phloroglucinol reductase) RN - I70C45KRO9 (2,4,6-trihydroxybenzaldehyde) SB - IM MH - Acetophenones/metabolism MH - Bacteria/chemistry/*enzymology/metabolism MH - Benzaldehydes/metabolism MH - Biocatalysis MH - Gallic Acid/analogs & derivatives/metabolism MH - Oxidoreductases Acting on CH-CH Group Donors/*chemistry/*metabolism MH - Protein Conformation MH - Substrate Specificity OTO - NOTNLM OT - dearomatization OT - enzyme catalysis OT - flavonoids OT - redox enzymes OT - reductases EDAT- 2016/11/23 06:00 MHDA- 2018/08/30 06:00 CRDT- 2016/11/23 06:00 PHST- 2016/08/02 00:00 [received] PHST- 2016/09/09 00:00 [revised] PHST- 2016/11/23 06:00 [pubmed] PHST- 2018/08/30 06:00 [medline] PHST- 2016/11/23 06:00 [entrez] AID - 10.1002/anie.201607494 [doi] PST - ppublish SO - Angew Chem Int Ed Engl. 2016 Dec 12;55(50):15531-15534. doi: 10.1002/anie.201607494. Epub 2016 Nov 22.