Reduction of salicylate to saligenin by Neurospora

Bachman, Daniel M.; Dragoon, Belle; John, Sosamma

doi:10.1016/0003-9861(60)90508-7

Cited by 20 publications

(9 citation statements)

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“…He found that benzaldehyde, cinnamaldehyde and anisaldehyde were dismuted to their respective acids and alcohols. In contrast Bachman, Dragoon & John (1960) obtained quantitative conversion of o-hydroxybenzoic to the corresponding alcohol by Neurospora crassa, while Polystictus versicolor reduced certain aromatic acids to the corresponding aldehydes and alcohols (Farmer, Henderson & Russell, 1959). The acids and alcohols found in the present work were intermediate products of metabolism and with time all trace of phenolic compounds disappeared.…”

Section: Discussioncontrasting

confidence: 41%

The Metabolism of Aromatic Compounds Related to Lignin by some Hyphomycetes and Yeast-like Fungi of Soil

Henderson¹

1961

Journal of General Microbiology

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SUMMARYThe metabolism of various lignin-related aromatic compounds by several soil Hyphomycetes and yeast-like fungi was investigated. Adaptation studies with whole organisms and cell-free extracts confirmed previously proposed metabolic pathways (Henderson & Farmer, 1955;Henderson, 1960). It was shown that protocatechuic acid is an intermediate in the metabolism of vanillin and ferulic acid. Protocatechuic acid oxidase activity of cell-free extracts of Pullularia pullulans was found to be stimulated by ferrous ions and to depend on -SH groups.

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Section: Discussioncontrasting

confidence: 41%

The Metabolism of Aromatic Compounds Related to Lignin by some Hyphomycetes and Yeast-like Fungi of Soil

Henderson¹

1961

Journal of General Microbiology

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“…Chemical methods for carboxylic acid reductions are limited, and they usually require prior derivatization and product deblocking with reactants containing competing functional groups. Biocatalytic reductions of carboxylic acids are attractive because the substrates are water soluble, blocking chemistry is not necessary, reductions are enantiospecific, and the scope of the reaction is very broad (24, 32).Although microbial reductions of carboxylic acids, usually producing the acids' corresponding aldehydes or alcohols, have been observed with whole-cell reactions of bacteria and fungi (3,4,6,8,20,22,24,25,30,(36)(37)(38)40), enzymatic reductions of carboxylic acids are relatively new and unexploited biocatalytic reactions of great potential value in organic synthesis (12).Aldehyde oxidoreductases, also known as carboxylic acid reductases (CAR), require ATP, Mg 2ϩ , and NADPH as cofactors (16,17,18,21,24). The reduction is a stepwise process involving initial binding of both ATP and the carboxylic acid to the enzyme in order to form mixed 5Ј-adenylic acid-carbonyl anhydride intermediates (9,15,25,27,39) that are subsequently reduced by hydride delivery from NADPH to form aldehyde products (16,25) (Fig.…”

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confidence: 99%

“…Although microbial reductions of carboxylic acids, usually producing the acids' corresponding aldehydes or alcohols, have been observed with whole-cell reactions of bacteria and fungi (3,4,6,8,20,22,24,25,30,(36)(37)(38)40), enzymatic reductions of carboxylic acids are relatively new and unexploited biocatalytic reactions of great potential value in organic synthesis (12).…”

mentioning

confidence: 99%

Nocardia sp. Carboxylic Acid Reductase: Cloning, Expression, and Characterization of a New Aldehyde Oxidoreductase Family

He¹,

Li²,

Daniels

et al. 2004

Appl Environ Microbiol

109

100

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We have cloned, sequenced, and expressed the gene for a unique ATP-and NADPH-dependent carboxylic acid reductase (CAR) from a Nocardia species that reduces carboxylic acids to their corresponding aldehydes. Recombinant CAR containing an N-terminal histidine affinity tag had K m values for benzoate, ATP, and NADPH that were similar to those for natural CAR, and recombinant CAR reduced benzoic, vanillic, and ferulic acids to their corresponding aldehydes. car is the first example of a new gene family encoding oxidoreductases with remote acyl adenylation and reductase sites.Aromatic, aliphatic, and alicyclic aldehydes and alcohols are useful intermediates in the chemical, pharmaceutical, and food industries. Chemical methods for carboxylic acid reductions are limited, and they usually require prior derivatization and product deblocking with reactants containing competing functional groups. Biocatalytic reductions of carboxylic acids are attractive because the substrates are water soluble, blocking chemistry is not necessary, reductions are enantiospecific, and the scope of the reaction is very broad (24, 32).Although microbial reductions of carboxylic acids, usually producing the acids' corresponding aldehydes or alcohols, have been observed with whole-cell reactions of bacteria and fungi (3,4,6,8,20,22,24,25,30,(36)(37)(38)40), enzymatic reductions of carboxylic acids are relatively new and unexploited biocatalytic reactions of great potential value in organic synthesis (12).Aldehyde oxidoreductases, also known as carboxylic acid reductases (CAR), require ATP, Mg 2ϩ , and NADPH as cofactors (16,17,18,21,24). The reduction is a stepwise process involving initial binding of both ATP and the carboxylic acid to the enzyme in order to form mixed 5Ј-adenylic acid-carbonyl anhydride intermediates (9,15,25,27,39) that are subsequently reduced by hydride delivery from NADPH to form aldehyde products (16,25) (Fig. 1). Aromatic CARs have been purified to homogeneity only from Neurospora (17) and Nocardia (21, 24) species. Although N-terminal and internal amino acid sequences were reported for our Nocardia enzyme (24), sequences have never been determined for any gene coding for CARs. CAR from Nocardia sp. strain NRRL 5646 has an extremely wide substrate range, and it enantiospecifically reduces carboxylic acids (8,24,32). We report here the cloning and expression of the first CAR gene, car, and the use of cloned enzyme in vitro and in vivo to reduce carboxylic acid substrates.Strains, plasmids, media, and growth. Bacteria and plasmids used in this study are listed in Table 1. Nocardia sp. strain NRRL 5646 (14) was grown at 30°C in Luria-Bertani (LB) medium containing 0.05% Tween 80 (vol/vol [liquid medium only]). With Escherichia coli as the recombinant host for pHAT-based vectors, cells were grown at 37°C on solid or in liquid LB medium. Ampicillin (100 g/ml) was incorporated into LB medium to select for recombinants, and isopropyl-␤-D-thiogalactopyranoside (IPTG) (1 mM) and/or 5-bromo-4-chloro-3-indolyl-␤-D-galactopyranosi...

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“…Mycelia of the fungus Neurospora crassa grown on culture media supplemented with salicylate are induced to form an enzyme catalyzing the reduction of a number of aromatic acids to the corresponding aldehydes [1,2]. This enzyme could be purified and characterized and was called aromatic reductase [3,4].…”

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confidence: 99%

Formation and Reduction of Intermediate Acyladenylate by Aryl‐Aldehyde

Gross

1972

European Journal of Biochemistry

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The enzyme aryl-aldehyde : NADP oxidoreductase catalyzes a rapid exchange of PPi and ATP. The reaction requires the presence of an aromatic acid and Mg2+ ions. The exchange reaction has a pH-optimum of approx. 8.5 and is inhibited by NADPH. The inhibition of the exchange reaction by hydroxylamine as well as the enzymic formation of benzoylhydroxamate confirm that an activated intermediate is involved in the reduction of aromatic acids. This compound was identified as acyladenylate which, however, is assumed not to exist in the free state under normal conditions. In a subsequent step the acyladenylate is reduced to aldehyde. This reaction depends on the presence of sulfhydryls and does not require Mg2+ ions. Both the activating and the reductive step are catalyzed by one enzyme.

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Reduction of salicylate to saligenin by Neurospora

Cited by 20 publications

References 9 publications

The Metabolism of Aromatic Compounds Related to Lignin by some Hyphomycetes and Yeast-like Fungi of Soil

The Metabolism of Aromatic Compounds Related to Lignin by some Hyphomycetes and Yeast-like Fungi of Soil

Nocardia sp. Carboxylic Acid Reductase: Cloning, Expression, and Characterization of a New Aldehyde Oxidoreductase Family

Formation and Reduction of Intermediate Acyladenylate by Aryl‐Aldehyde

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