Yeast Rhodotorula

Ring fission clearly occurs during the metabolism of phenol (Walker 1973) by the yeast Rhodotorula glutinis, and of aromatic acids by various fungi (Cain et al. 1968 Durham et al. 1984 Gupta et al. 1986). 

Gupta JK, C Jebsen, H Kneifel (1986) Sinapic acid degradation by the yeast Rhodotorula graminis. J Gen Microbiol 132 2793-2799. 

Unusual 2-ketoglutarate-dependent dioxygenations have been found in the yeast Rhodotorula glutinis ... 

One of the first reports on yeast-mediated color removal by a putative process of biosorption of azo dyes by yeast (Rhodotorula sp.) biomass belongs to [31]. Yeast species such as Kluveromyces marxianus removed the diazo dye remazol black B [10], Candida catenulata and Candida kefyr removed more than 90% of amaranth by biosorption [6]. Biosorption uptake of the textile azo dyes remazol blue, reactive black, and reactive red by S. cerevisiae and C. tropicalis varied according to the selected dye, dye concentration, and exposure time [5, 7]. In a recent screening work carried out by [32], from the 44 yeast strains tested for their decolorization ability, 12 of them removed the dye Reactive Brilliant Red K-2BP by biosorption, among them the following were identified S. cerevisiae, Saccharomyces uvarum, Torulopsis Candida, and Saccharomycopsis lipolytica. 

Gupta JK, Sharma P, Kern HW et al (1990) Degradation of synthetic lignins and some lignin monomers by the yeast Rhodotorula glutinis. World J Microb Biotechnol 6 53-58... 

The use of D-AAO from the yeast Rhodotorula gracilis to deracemize naphthyl amino acids has been studied in some detail by the groups of Servi and Pollegioni, who compared the kinetic properties of the enzyme with racemic 1- and 2-naphthylalanine (1 and 2) and 1- and 2-naphthylglycine (3 and 4). 

An analog of the (6S)-methylketosulfone towards Trusopt , 5,6 dihydro-(6S)-pro-pyl-4H-thieno[2,3fc]thiopyran-4-one 7,7-dioxide ( ketosulfone , Figure 13.28), the precursor to the carbonic anhydrase inhibitor L-683393 (Merck), could be reduced to the trans-hydroxysulfone 5,6 dihydro-(4S)-hydroxy-(6S)-propyl-4H-thieno[2,3F] thiopyran 7,7-dioxide by whole cells of the yeast Rhodotorula rubra MY 2169 from the Merck collection (Lorraine, 1996). Low water-solubility limited the optimum substrate concentration to 2 g L, as organic solvents added to increase solubility resulted in lower rates, which at 0.04 g (g dew)-1 h 1 were not high to start with. Diastereomeric excess ranged from 89 to 94% d.e., and decreased with increasing conversion. 

K. Lorraine, S. King, R. Greasham, and M. Chartrain, Asymmetric bioreduction of a ketosulfone to the corresponding trans-hydroxysulfone by the yeast Rhodotorula rubra MY 2169, Enzyme Microb. Technol. 1996, 39, 250-255. 

Another yeast, Rhodotorula rubra MY 2169, has been shown to reduce a ketosulfone 8 to the corresponding tram-hydroxysulfone 9 (Scheme 19.8). This hydroxysulfone is an intermediate in the drug candidate L-685,393 (10), a carbonic anhydrase inhibitor.81 Results of this biotransformation yielded gram quantities of product with a de of >96%. Studies by Zeneca discuss additional screening experiments aimed at finding microorganisms to reduce a similar ketosulfone.82... 

Boekhout T, Fell JW, Fonseca A, Prillinger H, Lopandic K, Roeijmans H The basidiomycetous yeast Rhodotorula yarmwii comb. nov. Antonie Van Leeuwenhoek 2000 77 355-358. 

Figure 5 Kinetics of transport of D- and L-xylose in the yeast Rhodotorula gracilis. [Adapted from Dusinsky (I).]...

Salmonella, Vibrio parahaemolyti-cus, Clostridium botulinum, Serra-tia, Lactobacillus, Pediococcus, some molds, yeasts (Rhodotorula, Pichia) Some cheeses (cheddar, swiss, muenster, provolone), cured meat (ham), some fruit juice concentrates foods containing 55% (w/ w) sucrose or 12% sodium chloride. 

Perhaps the earliest triple helicate 48 to be characterized, however, is that formed with rhodotorulic acid 46 (HaL ), the dihydroxamate siderophore produced by the yeast Rhodotorula pilimanae [75,76], Subsequently, a related synthetic iron(III) triple helicate 49 based on diprotic tetradentate 1,2-hydroxypyridinone 47 (H2L ) was synthesized (Scheme 5) and characterized by an X-ray structure analysis. 

The phenol-assimilating yeast C. maltosa degraded a number of phenols even though these were unable to support growth hydroxylation of 3-chloro- and 4-chlorophenol produced initially 4-chlo-rocatechol and then 5-chloropyrogallol (Polnisch et al. 1992). The yeast Rhodotorula cresolica was able to assimilate phenol, 3- and 4-methylphenol, catechol and 3- and 4-methylcatechol, resorcinol... 

Highly functionalized 2-alkoxycarbonylcyclopentanones can also be selectively reduced, although with (+ )-4-benzyloxycarbonyl-4-hydroxy-2-methoxycarbonyl-3-methyl-2-cyclopen-ten-l-one (6) the yeast Rhodotorula rubra is superior to baker s yeast161. 

Comments Ciypfococcusis a non-fermenting yeast with alliances to some Ascomycetes Torula (Black Yeast), Rhodotorula (Red Yeast) and Candida. 

An iron(III)-binding compound with the properties of a secondary hydroxamic acid has been isolated from supernatant solutions of iron-deficient cultures of a red yeast, Rhodotorula pilimanae (Atkin and Neilands, 1968). The compound rhodotorulic acid (CXVIII) was characterized as LL-3,6-bis (JV-acetyl-3-hydroxyaminopropyl)-2, 5-piperazinedione, i.e., the diketopiperazine of -JV-acetyl-L-5-N-hydroxyomithine. The latter is an amino acid which is a constituent of ferrichromes, albomycins, and fusarinines. In the characterization of rhodotorulic acid, IR, UV, NMR, ORD, and mass spectroscopy were applied. 

In the environment, bacteria that have the ability to degrade PAHs have been reported. Saprotrophic soil fungi Pusarium solani, and yeast Rhodotorula glutinis metabolize pyrene as a sole source of carbon. Mushroom compost is reported to be used directly to ameliorate phenathrene contaminated soil. After 111 days incubation time, 36.7+2.9% loss of soil-associated phenanthrene was observed. Exposure of... 

Enterobacteria are mentioned. In addition, the yeasts Rhodotorula glutinis and Cryptococcus albidus, as well as the molds Geotrichum candidum and Aureobasid-ium pullulans, are named. 

Torularhodin, a characteristic pigment of red yeast (Rhodotorula spp.), contains a carboxylic acid group at one end. A scheme for the biosynthesis of this compound from j8-zeacarotene has been proposed, but experimental evidence on this point is not available (Britton, 1976a). 

Temperature effects on carotenoid biosynthesis have been observed with F. aquaeductuum and N. crassa. Quantitative effects are observed in Phy-comyces and the yeasts Rhodotorula rubra and R. penaus. Qualitative changes have been observed in Rhodotorula glutinis. In ripening tomatoes, the synthesis of lycopene, but not /3-carotene, is inhibited in firuit held above 30°C (Goodwin and Jamikom, 1952 Tomes et al., 1956 Czygan and Wil-luhn, 1%7). However, the amount of /3-carotene formed in these fruits is relatively small. 

Newly isolated unidenti ed red yeast, Rhodotorula sp., converted (+)-limonene (68) mainly to (+)-limonene-l,2-tran5 -diol (71a), (-r)-trfl 5 -carveol (81a), (+)-cis-carveol (81b), and (+) carvone (93 ) together with (+) limonene-1,2 cis-diol (71b) as minor product (Noma and Asakawa, 2007b) (Figure 19.36). 

FIGURE 19.36 Biotransformation of (+)-limonene (68) by red yeast, Rhodotorula sp. and Cladosporium sp. T7. (Modi ed from Mukherjee, B.B. et al., Appl. Microbiol, 25, 447, 1973 Noma, Y. and Asakawa, Y Microbial transformation of limonene and related compounds. Proceedings of 51st TEAC, 2007b, pp. 299-301.)... 

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