The Oxidation of Glucose and Related Compounds by Glucose Oxidase from Aspergillus niger<sup>*</sup>

Pazur, John H.; Kleppe, Kjell

doi:10.1021/bi00892a018

Cited by 239 publications

(125 citation statements)

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Section: Discussionmentioning

confidence: 99%

“…GOX catalyzes the oxidation of d-Glc to d-gluconic acid and hydrogen peroxide (Pazur and Kleppe, 1964). The best characterized form of the enzyme, from the fungi Aspergillus niger, is a homodimer, contains two non-covalently bound molecules of FAD, and is highly specific for Glc (Pazur and Kleppe, 1964). The functionally equivalent hexose oxidase (HOX) from the red algae Chondrus crispus can use multiple mono-and disaccharides, lacks FAD, and likely requires copper for activity (Hansen and Stougaard, 1997).…”

Section: Discussionmentioning

confidence: 99%

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Tobacco Nectarin V Is a Flavin-Containing Berberine Bridge Enzyme-Like Protein with Glucose Oxidase Activity

2004

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Ornamental tobacco (Nicotiana langsdorffii X N. sanderae) secretes a limited array of proteins (nectarins) into its floral nectar. Careful sodium dodecyl sulfate-polyacrylamide gel electrophoresis analysis of tobacco nectar revealed that a broad protein band from 61 to 65 kD actually consists of five discrete protein bands. N-terminal sequencing and tryptic peptide mass spectrometry fingerprint analysis demonstrated that the upper three bands are isoforms of the same protein, NEC5 (Nectarin V), whereas the lower two bands, NEC4 (Nectarin IV), are related to each other but not to NEC5. Reverse transcriptionpolymerase chain reaction (RT-PCR) based upon N-terminal sequence of NEC5 generated a short cDNA that encoded the N terminus of the NEC5 protein. Two rounds of inverse-PCR using genomic DNA permitted the isolation of approximately one-half of the coding region of the nec5 gene along with 787 nucleotides of the 5Ј-flanking region. This DNA fragment was used as a probe to isolate a near full-length nec5 clone from a nectary-derived cDNA library. BLAST analysis identified the nec5 cDNA as a berberine bridge enzyme-like protein. Approximately 40% of the cDNA sequence corresponded to peptides that were identified by tryptic peptide mass spectrometry fingerprint analysis of the NEC5 protein, thereby confirming that this cDNA encoded the NEC5 protein.In-gel assays also demonstrated that NEC5 contains a covalently linked flavin, and it possesses glucose oxidase activity. RT-PCR-based expression analyses showed that nec5 expression is limited exclusively to the nectary gland during late stages of floral development.During evolution, many angiosperms have developed a remarkable reproductive strategy that relies on animal pollinators to transfer pollen between plants. These plants attract pollinators with floral rewards that encourage insect, avian, and mammalian visitors. Perhaps the primary reward for many species that visit angiosperms is floral nectar. Floral nectar is produced from a terminally differentiated organ frequently located at the base of the flower. Nectar is principally an aqueous carbohydrate solution, containing most frequently sucrose, glucose, and fructose. However, nectars are also known to contain amino acids (Baker and Baker, 1973), organic acids Baker, 1975), vitamins (Griebel andHess, 1940), oils (Vogel, 1969), biological cations (Heinrich, 1989), and proteins (Carter et al., 1999; Thornburg, 2000, 2003;Thornburg et al., 2003).Over the past 5 years, our work has demonstrated the presence of a limited array of five proteins, termed nectarins, that are secreted into the nectar of ornamental tobacco (N. langsdorffii X N. sanderae) (Carter et al., 1999). We have demonstrated that the major protein, NEC1 (Nectarin I), is a novel germinlike protein (Carter et al., 1999) that functions as a superoxide dismutase, producing high levels (up to 4 mm) of hydrogen peroxide (Carter and Thornburg, 2000). These levels are antimicrobial (C. Carter and R.W. Thornburg, unpublished data) and have led to the hypothe...

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Tobacco Nectarin V Is a Flavin-Containing Berberine Bridge Enzyme-Like Protein with Glucose Oxidase Activity

2004

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“…The nitrogen atoms found in heterocyclic aromatic systems may be classified into those of the pyridine type " (1) and N(5) of the oxidized flavin] and those of the pyrrole type " (3) and N(10) of the oxidized flavin]. The two types react differently to the formation of hydrogen bonds.…”

Section: N-nmr Studies On Oxidized Glucose Oxidasementioning

confidence: 99%

¹⁵N‐ and ¹³C‐NMR investigations of glucose oxidase from Aspergillus niger

Sanner

Macheroux

Rüterjans

et al. 1991

European Journal of Biochemistry

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The apoprotein of glucose oxidase from Aspergillus niger was reconstituted with specifically lSN-and 13C-enriched FAD derivatives and investigated by "N-and I3C-NMR spectroscopy. On the basis of the "N-NMR results it is suggested that, in the oxidized state of glucose oxidase, hydrogen bonds are formed to the N(3) and N(5) positions of the isoalloxazine system. The hydrogen bond to N(3) is more pronounced than that to N(5) as compared with the respective hydrogen bonds formed between FMN and water. The resonance position of N(10) indicates a small decrease in spz hybridization compared to free flavin in water. Apparently the isoalloxazine ring is not planar at this position in glucose oxidase.Additional hydrogen bonds at the carbonyl groups of the oxidized enzyme-bound FAD were derived from the I3C-NMR results. A strong downfield shift observed for the C(4a) resonance may be ascribed in part to the decrease in sp2 hybridization at the N(10) position and to the polarization of the carbonyl groups at C(2) and C(4). The polarization of the isoalloxazine ring in glucose oxidase is more similar to FMN in water than to that of tetraacetyl-riboflavin in apolar solvents.In the reduced enzyme the N(l) position is anionic at pH 5.6. The pK, is shifted to lower pH values by at least 1 owing to the interaction of the FAD with the apoprotein.As in the oxidized state of the enzyme, a hydrogen bond is also

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“…The D or L configuration of glucose and galactose was determined with D-glucose oxidase or D-galactose oxidase and peroxidase (21,25). The enzymatic analysis indicated that both glucose and galactose in PS-2 had the D configuration (data not shown).…”

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confidence: 99%

Isolation and structural analysis of polysaccharide containing galactofuranose from the cell walls of Bifidobacterium infantis

1996

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We isolated cell wall polysaccharides (PS-1 and PS-2) from Bifidobacterium infantisBifidobacteria are anaerobic gram-positive bacteria and are believed to be associated with health-promoting effects in the host intestine. Recent studies with several Bifidobacterium strains have offered structural information concerning the cell surface construction, such as lipoteichoic acids (4,5,10,18), teichoic acids (26), and cell wall polysaccharides (7,17). Op den Camp et al. have isolated from Bifidobacterium bifidum a new type of lipoteichoic acid, containing a 1,2-linked polyglycerophosphate backbone between a glycolipid moiety and a linear polysaccharide, and found a unique structure, 1,5-linked ␤-D-galactofuranose homopolymer (galactofuranan), in the polysaccharide chain (18). On the other hand, Fischer et al. have provided another structure for lipoteichoic acid-like amphipathic polymers, which consist of a glycolipid moiety, 1,6-linked ␤-glucan, and 1,5-linked ␤-galactofuranan with side chains of monomeric glycerophosphate (4, 5). Such macroamphiphiles do not link to peptidoglycan but are considered to be anchored to membranes through their lipid moiety and should be common in several species of Bifidobacterium (10).Previously, we reported the carbohydrate composition of purified cell walls of Bifidobacterium infantis Reuter ATCC 15697 (24). In the present study, we isolated two distinct neutral polysaccharides, PS-1 and PS-2, from the purified cell walls of the same strain and found that the backbone of PS-2 is a 1,3-linked galactan consisting of ␤-D-galactofuranose and ␣-Dgalactopyranose in which more than 90% of the ␤-D-galactofuranosyl residues and about 30% of ␣-D-galactopyranosyl residues are occupied by ␤-D-glucopyranose at position 6. The backbone structure, 33)-␤-D-Gal f -(133)-␣-D-Gal p -(13, has been identified also in the lipopolysaccharide of Klebsiella pneumoniae (12-15, 27, 28), Pasteurella haemolytica (22, 23), Serratia marcescens (19,20), and Serratia plymuthica (1). It is of interest that the cell wall polysaccharide from B. infantis contains the same structure as O-specific antigen of some gramnegative bacteria.Preparation and carbohydrate composition of cell wall polysaccharides, PS-1 and PS-2. We previously described the growth conditions of B. infantis and the isolation procedure of purified cell walls (24). Determinations of amino acids, monosaccharides, fatty acids, and nucleic acids of the cell walls were also carried out by the same methods as previously reported (24). B. infantis cell walls consisted of neutral sugars (glucose and galactose), amino sugars (glucosamine and muramic acid), peptidoglycan-derived amino acids (alanine, glutamic acid, threonine, serine, and ornithine), and a small amount of fatty acids, so that they were considered to be free from contamination with nucleic acids and proteins (24).The purified cell walls (300 mg) were treated with 5% trichloroacetic acid at 4ЊC overnight and then centrifuged, and the supernatant was thoroughly dialyzed against deionized water. T...

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The Oxidation of Glucose and Related Compounds by Glucose Oxidase from Aspergillus niger^*

Cited by 239 publications

References 16 publications

Tobacco Nectarin V Is a Flavin-Containing Berberine Bridge Enzyme-Like Protein with Glucose Oxidase Activity

Tobacco Nectarin V Is a Flavin-Containing Berberine Bridge Enzyme-Like Protein with Glucose Oxidase Activity

¹⁵N‐ and ¹³C‐NMR investigations of glucose oxidase from Aspergillus niger

Isolation and structural analysis of polysaccharide containing galactofuranose from the cell walls of Bifidobacterium infantis

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The Oxidation of Glucose and Related Compounds by Glucose Oxidase from Aspergillus niger*

Cited by 239 publications

References 16 publications

Tobacco Nectarin V Is a Flavin-Containing Berberine Bridge Enzyme-Like Protein with Glucose Oxidase Activity

Tobacco Nectarin V Is a Flavin-Containing Berberine Bridge Enzyme-Like Protein with Glucose Oxidase Activity

15N‐ and 13C‐NMR investigations of glucose oxidase from Aspergillus niger

Isolation and structural analysis of polysaccharide containing galactofuranose from the cell walls of Bifidobacterium infantis

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The Oxidation of Glucose and Related Compounds by Glucose Oxidase from Aspergillus niger^*

¹⁵N‐ and ¹³C‐NMR investigations of glucose oxidase from Aspergillus niger