scholarly journals Aspects of the stereochemistry of torularhodin biosynthesis

1970 ◽  
Vol 117 (5) ◽  
pp. 921-927 ◽  
Author(s):  
R. E. Tefft ◽  
T. W. Goodwin ◽  
K. L. Simpson
Keyword(s):  
Mevalonic Acid ◽  
Rhodotorula Glutinis ◽  
Experimental Techniques ◽  
Rhodotorula Rubra ◽  
Isopentenyl Pyrophosphate ◽  
A Value ◽  
Dimethylallyl Pyrophosphate

1. The incorporation of [2-14C]acetate, [2-14C]mevalonic acid and [2-14C,2-3H2]-mevalonic acid into torulene and torularhodin by Rhodotorula rubra and Rhodotorula glutinis was studied. 2. A recovery of 14.3% of the label was obtained on decarboxylation of the torularhodin biosynthesized from [2-14C]mevalonic acid. 3. An analysis of the 3H/14C ratio in torularhodin gave a value of 9.44:8. 4. These results, obtained by different experimental techniques, show that the reactions in the conversion of the dimethyl group of isopentenyl pyrophosphate into the 16′,17′-position of torularhodin must be free from randomization. A mechanism for the isomerization of isopentenyl pyrophosphate to dimethylallyl pyrophosphate is suggested.

scholarly journals The isoprenoid alcohol pathway, a synthetic route for isoprenoid biosynthesis

2019 ◽  
Vol 116 (26) ◽  
pp. 12810-12815 ◽  
Author(s):  
James M. Clomburg ◽  
Shuai Qian ◽  
Zaigao Tan ◽  
Seokjung Cheong ◽  
Ramon Gonzalez
Keyword(s):  
Energy Efficient ◽  
Sole Carbon Source ◽  
Isoprenoid Biosynthesis ◽  
High Flux ◽  
Alternative Route ◽  
Synthetic Route ◽  
Isopentenyl Pyrophosphate ◽  
Commodity Chemicals ◽  
Central Carbon ◽  
Dimethylallyl Pyrophosphate

The more than 50,000 isoprenoids found in nature are all derived from the 5-carbon diphosphates isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). Natively, IPP and DMAPP are generated by the mevalonate (MVA) and 2-C-methyl-d-erythritol-4-phosphate (MEP) pathways, which have been engineered to produce compounds with numerous applications. However, as these pathways are inherently constrained by carbon, energy inefficiencies, and their roles in native metabolism, engineering for isoprenoid biosynthesis at high flux, titer, and yield remains a challenge. To overcome these limitations, here we develop an alternative synthetic pathway termed the isoprenoid alcohol (IPA) pathway that centers around the synthesis and subsequent phosphorylation of IPAs. We first established a lower IPA pathway for the conversion of IPAs to isoprenoid pyrophosphate intermediates that enabled the production of greater than 2 g/L geraniol from prenol as well as limonene, farnesol, diaponeurosporene, and lycopene. We then designed upper IPA pathways for the generation of (iso)prenol from central carbon metabolites with the development of a route to prenol enabling its synthesis at more than 2 g/L. Using prenol as the linking intermediate further facilitated an integrated IPA pathway that resulted in the production of nearly 0.6 g/L total monoterpenoids from glycerol as the sole carbon source. The IPA pathway provides an alternative route to isoprenoids that is more energy efficient than native pathways and can serve as a platform for targeting a repertoire of isoprenoid compounds with application as high-value pharmaceuticals, commodity chemicals, and fuels.

scholarly journals Development of the activities of enzymes of the isoprenoid pathway during early stages of pea-seed germination

1972 ◽  
Vol 130 (4) ◽  
pp. 983-995 ◽  
Author(s):  
T. R. Green ◽  
D. J. Baisted
Keyword(s):  
Seed Germination ◽  
Initial Increase ◽  
Mevalonate Kinase ◽  
Isopentenyl Pyrophosphate ◽  
Isoprenoid Pathway ◽  
Dimethylallyl Pyrophosphate ◽  
Rate Limiting ◽  
Pea Seed ◽  
Germination Stage ◽  
Squalene Synthetase

The activities of individual enzymes of the isoprenoid pathway from mevalonate kinase to squalene synthetase in homogenates of seeds germinated up to 32h were assayed. Changes in the activity of each enzyme were observed and compared with the activity at the 2h germination stage. Activities of alkaline phosphatase and fructose 1,6-diphosphate aldolase were similarly measured to provide a reference for changes in the general metabolic activity of seeds during imbibition of water. Water uptake reached a plateau after 12h. The reference enzymes almost doubled in activity between 2 and 8h and thereafter their activities steadily declined. All of the enzymes of the isoprenoid pathway increased in activity between 2 and 6h and, thereafter, with the exception of the prenyltransferase, their activities remained relatively constant. With the prenyltransferase activity the initial increase was followed by a short plateau between 6 and 9h and then a second increase to a maximum between 14 and 16h. After 16h the activity declined. The relative activities of the isoprenoid enzymes at 16h of germination were mevalonate kinase>phosphomevalonate kinase>pyrophosphomevalonate decarboxylase≈isopentenyl pyrophosphate isomerase>squalene synthetase>isopentenyl pyrophosphate/dimethylallyl pyrophosphate prenyltransferase. The finding that the prenyltransferase may be the rate-limiting enzyme in squalene synthesis from mevalonate is discussed in relation to regulation of isoprenoid synthesis during pea-seed germination.

scholarly journals QM/MM studies of the type II isopentenyl diphosphate–dimethylallyl diphosphate isomerase demonstrate a novel role for the flavin coenzyme

RSC Advances ◽  
2017 ◽  
Vol 7 (36) ◽  
pp. 22286-22293
Author(s):  
Qianqian Hou ◽  
Kang Wang ◽  
Feng Xu ◽  
Wenshen Zhang ◽  
Kejian Ji ◽  
...  
Keyword(s):  
Isopentenyl Diphosphate ◽  
Type Ii ◽  
Isopentenyl Pyrophosphate ◽  
Dimethylallyl Diphosphate ◽  
Dimethylallyl Pyrophosphate

The type II isopentenyl diphosphate:dimethylallyl diphosphate isomerase (IDI-2) catalyzes the reversible isomerization of isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP).

scholarly journals Biosynthesis of geraniol and nerol and their β-d-glucosides in Perlargonium graveolens and Rosa dilecta

1972 ◽  
Vol 130 (4) ◽  
pp. 1045-1054 ◽  
Author(s):  
Derek V. Banthorpe ◽  
Geoffrey N. J. Le Patourel ◽  
Martin J. O. Francis
Keyword(s):  
Double Bond ◽  
Hydrogen Atom ◽  
Higher Plants ◽  
Animal Tissue ◽  
Labelling Pattern ◽  
Isopentenyl Pyrophosphate ◽  
Pelargonium Graveolens ◽  
Dimethylallyl Pyrophosphate

1. 3R-[2-14C]Mevalonate was incorporated into geranyl and neryl β-d-glucosides in petals of Rosa dilecta in up to 10.6% yield, and the terpenoid part was specifically and equivalently labelled in the moieties derived from isopentenyl pyrophosphate and 3,3-dimethylallyl pyrophosphate. A similar labelling pattern, with incorporations of 0.06–0.1% was found for geraniol or nerol formed in leaves of Pelargonium graveolens The former results provide the best available evidence for the mevalonoid route to regular monoterpenes in higher plants. 2. Incorporation studies with 3RS-[2-14C,(4R)-4-3H1]-mevalonate and its (4S)-isomer showed that the pro-4R hydrogen atom of the precursor was retained and the pro-4S hydrogen atom was eliminated in both alcohols and both glucosides. These results suggest that the correlation of retention of the pro-4S hydrogen atom of mevalonate with formation of a cis-substituted double bond, such as has been found in certain higher terpenoids, does not apply to the biosynthesis of monoterpenes. It is proposed that either nerol is derived from isomerization of geraniol or the two alcohols are directly formed by different prenyltransferases. Possible mechanisms for these processes are discussed. 3. The experiments with [14C,3H]mevalonate also show that in these higher plants, as has been previously found in animal tissue and yeast, the pro-4S hydrogen atom of mevalonate was lost in the conversion of isopentenyl pyrophosphate into 3,3-dimethylallyl pyrophosphate.

Stereochemistry of isopentenyl pyrophosphate isomerase

1972 ◽  
Vol 182 (1068) ◽  
pp. 277-295 ◽  
Keyword(s):  
Acetic Acid ◽  
Deuterium Oxide ◽  
Mevalonic Acid ◽  
Methyl Groups ◽  
Farnesyl Pyrophosphate ◽  
Soluble Enzyme ◽  
Pig Liver ◽  
Isopentenyl Pyrophosphate ◽  
Prototropic Isomerization ◽  
Preliminary Communication

Mevalonic acid stereospecifically labelled with tritium in the 2-position was incubated, in a deuterium oxide medium containing adenosine triphosphate, with a soluble enzyme pre­paration from pig liver; and so converted into farnesyl pyrophosphate. This was hydrolysed enzymically to farnesol which was oxidized, by ozone followed by sodium hypoiodite, to acetic acid originating from the terminal isopropylidene group of farnesol. The tritium in this acetic acid was found, on analysis by a recently developed enzymic method, to be present largely in chiral methyl groups the chirality of which was R or S according to the chirality at C-2 of the parent mevalonic acid. It is deduced that these chiral methyl groups were formed on the enzyme isopentenyl pyrophosphate isomerase, by addition of a deuteron from the medium to the 3 re , 4 re face of the double bond in isopentenyl pyrophosphate. The stereo­chemical relationship between the added and abstracted hydrogen in the prototropic isomerization mediated by this enzyme is thereby established. A preliminary communication of these results has been made (Clifford, Cornforth, Mallaby & Phillips 1971).

scholarly journals Мікробіологічна та вірусологічна характеристика морської води Одеської затоки та акваторії острова Зміїний

2021 ◽  
Author(s):  
Т. В. Гудзенко ◽  
О. Г. Горшкова ◽  
О.В. Волювач ◽  
Н.Ю. Васильєва ◽  
Г.В. Лісютін ◽  
...  
Keyword(s):  
Candida Albicans ◽  
Salmonella Typhimurium ◽  
Cryptococcus Neoformans ◽  
Rhodotorula Glutinis ◽  
Cryptococcus Albidus ◽  
Rhodotorula Rubra

Проведені комплексні мікробіологічні, вірусологічні, санітарно–екологічні та генетичні дослідження морської води Одеської затоки Чорного моря та акваторії острова Зміїний дозволили виявити мікробіологічне (умовно-патогенні, санітарно-показові бактерії, віруси) та хімічне (важкі метали, нафтопродукти, ПАР та інше) забруднення в контактній зоні моря. У морської води акваторії острова Зміїний як в прибережній зоні, так і на відстані 100 м від берега, незважаючи на сильний нагонний вітер та морське хвилювання, були виявлені патогенні для людини віруси гепатиту А і ротавірусу. Вперше з акваторії острова Зміїний виділено та ідентифіковано 7 видів дріжджів з 5 родів (Cryptococcus albidus, Cryptococcus neoformans, Aerobasidium pullulans, Candida albicans, Rhodotorula rubra, Rhodotorula glutinis, Rhodosporidium paludigenum). Домінування видів чорної та рожевої дріжджової мікробіоти є характерним для водних екосистем. Встановлено високий індекс таксономічної різноманітності - 10 родів домінуючих бактерій в морській воді Одеської затоки Чорного моря. Вперше було встановлено, що до складу домінуючих гетеротрофних бактерій входять представники малодослідженої групи ковзних бактерій, що беруть участь у процесах деструкції і мінералізації складних природних та синтетичних сполук в морському середовищі в умовах хронічного антропогенного забруднення, зокрема в акваторії Одеського заливу найбільш забрудненої побутовими стоками - в районі Дачі Ковалевського. Ліполітичні бактерії, здатні брати участь у процесах самоочищення морського середовища, виявлено в прибережній зоні о. Зміїний. Найбільша чисельність тіонових бактерій була зерєєстрована в районі Дачі Ковалевського - у місці із сильним антропогенним навантаженням по синтетичним поверхнево-активним речовинами, Сu(II), Ct(VI), Zn(II) та сезонно по нафтопродуктам. У бактеріальних тест-системах Salmonella typhimurium ТА100 та Salmonella typhimurium ТА98 встановлений генотиксичний та мутагенний потенціал забруднення морської води Одеського узбережжя та акваторії острову Зміїний.

DETERIORAÇÃO DE REFRIGERANTES POR LEVEDURAS

2004 ◽  
Vol 5 (2) ◽  
Author(s):  
C. D. Rocha ◽  
H. J. Schmidt ◽  
C. Monteiro ◽  
E. Odebrecht
Keyword(s):  
Soft Drink ◽  
Debaryomyces Hansenii ◽  
Rhodotorula Glutinis ◽  
Cryptococcus Laurentii ◽  
Rhodotorula Mucilaginosa ◽  
Candida Lipolytica ◽  
Rhodotorula Rubra ◽  
Zygosaccharomyces Bailii ◽  
Candida Sp ◽  
Saccharomycodes Ludwigii

Refrigerantes são bebidas não alcoólicas carbonatadas e constituem ótima fonte de glicídios. A composição química adocicada, o pH menor que 4,3, a aw maior que 0,90 e a atmosfera dos refrigerantes oferece condições favoráveis ao desenvolvimento de diversos microrganimos, incluindo leveduras deteriorantes..A deterioração ocasionada nos refrigerantes não constitui um risco à saúde das pessoas, mas este fenômeno prejudica a imagem de fábricas de refrigerantes, como também pode causar sérias perdas econômicas..Essas perdas podem ser minimizadas com o rastreamento da origem dos focos de contaminação, bem como conhecendo o risco potencial que cada levedura representa para o produto..As leveduras comumente detectadas em bebidas não alcoólicas carbonatadas, são as Brettanomyces sp, Candida lipolytica, Candida sp, Criptococcus albidus, Cryptococcus laurentii, Debaryomyces hansenii, Hanseniaspora sp, Hansenula sp, Kloeckera sp, Kluyveromyces sp, Zygosaccharomyces bailii, Zygosaccharomyces rouxii, Rhodotorula mucilaginosa, Rhodotorula glutinis, Rhodotorula rubra, Pichia sp, Saccharomyces cerevisae, Saccharomyces sp.,Saccharomycodes ludwigii, Schizosaccharomyces sp, e Zygosaccharomyces sp. SOFT DRINK DETERIORATION BY YEASTS Abstract Soft drinks are non alcoholic carbonated beverages that become an excellent source of glycids. Sugar composition, pH lower than 4.3, aw higher than 0.90 and atmosphere of soft drinks are conditions that contribute for the development of many microorganisms, including spoilage yeasts. Soft drink deterioration is not a health risk for people, but this phenomenon damages the beverage companies image and can yield serious economic damages. This problem could be reduced knowing the contamination focus origin, and also understanding the potential risk that each yeast represents to the product. The common yeasts found in nonalcoholic carbonated beverages are Brettanomyces sp, Candida lipolytica, Candida sp, Criptococcus albidus, Cryptococcus laurentii, Debaryomyces hansenii, Hanseniaspora sp, Hansenula sp, Kloeckera sp, Kluyveromyces sp, Zygosaccharomyces bailii, Zygosaccharomyces rouxii, Rhodotorula mucilaginosa, Rhodotorula glutinis, Rhodotorula rubra, Pichia sp, Saccharomyces cerevisae Saccharomyces sp, Saccharomycodes ludwigii, Schizosaccharomyces sp and Zygosaccharomyces sp.

A Crystallographic Investigation of Phosphoantigen Binding to Isopentenyl Pyrophosphate/Dimethylallyl Pyrophosphate Isomerase

2005 ◽  
Vol 127 (2) ◽  
pp. 536-537 ◽  
Author(s):  
Johan Wouters ◽  
Fenglin Yin ◽  
Yongcheng Song ◽  
Yonghui Zhang ◽  
Yamina Oudjama ◽  
...  
Keyword(s):  
Crystallographic Investigation ◽  
Isopentenyl Pyrophosphate ◽  
Dimethylallyl Pyrophosphate
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